21

iuc c|cpicr
Nciurc cn! ccmpcsiiicn
c| crgcnic cci!s
2.1 Gcncrc| c|crccicrizciicn
Organic acids aro lypicaI producls of microbiaI molaboIism. AII organic
acids occur naluraIIy in a varioly of vogolabIo and animaI subslralos and
can, lloroforo, bo oillor naluraIIy prosonl as consliluonls of foods as a
rosuIl of normaI bioclomicaI molaboIic procossos, dirocl addilion as acid-
uIanls, lydroIysis, or bacloriaI grovll, or can Ialor bo addod diroclIy or
indiroclIy lo llo producls (Gomis, 1992).
An organic acid is an organic compound vill acidic proporlios and
conlaining carbon, as do aII organic compounds. Tlo mosl common
organic acids aro llo carboxyIic acids vloso acidily is associalod vill
lloir carboxyI group ÷COOH. Tloso aro gonoraIIy voaI acids, vloroas
suIfonic acids, conlaining llo group OSO
3
H, aro roIalivoIy slrongor acids.
Tlo acidily of an acid is dolorminod by llo roIalivo slabiIily of llo conju-
galo baso of llo acid, aIllougl ollor groups can aIso confor acidily. Tlis
acidily is, lovovor, usuaIIy voaI and is llo rosuIl of llo ÷OH, ÷SH, onoI
group, and llo plonoI group (Iiguro 2.1) (Tloron and Iuos, 2007).
Organic acids do nol dissocialo compIoloIy in valor as opposod lo
llo slrong minoraI acids. AIllougl llo Iovor moIocuIar voigll acids sucl
as formic and acolic acids aro valor soIubIo, llo liglor moIocuIar voigll
organic acids sucl as bonzoic acid, aro insoIubIo in llo moIocuIar (noulraI)
form. Mosl organic acids aro, lovovor, vory soIubIo in organic soIvonls.
Ixcoplions lo llis soIubiIily may bo provaIonl in llo prosonco of ollor sub-
sliluonls llal may lavo an offocl on llo poIarily of llo compound (Tloron
and Iuos, 2007).
Organic acids lavo llo common donominalor of laving carbon in
lloir slrucluro, and aIllougl Ioss roaclivo llan inorganic acids, lloy aro
abIo lo dissoIvo minoraIs in llo minoraI rosorvo in llo soiI. Organic acids
llal lavo 10 or fovor carbons in lloir slrucluro, aro dislinguislod from
fally acids llal, on llo ollor land, lavo slraigll carbon ovon-numbor
clains of 12 lo 24. Organic acids oxisl in lvo basic forms: puro acids or
bufforod acids. IncIudod in llo puro acids aro Iaclic acid, propionic acid,
acolic acid, cilric acid, and bonzoic acid, vloroas llo caIcium and sodium
saIls of propionic, acolic, cilric, and bonzoic acids aro bufforod organic
22 Orgcnic Aci!s cn! Icc! Prcscrtciicn
acids. Tloso bufforod organic acids aro safor lo landIo and Ioss causlic
lo maclinory (Hoffman and Iossin, 2000). Mosl organic acids lavo an
advanlago bocauso of lloir simpIo slrucluro and smaII moIocuIar sizo or
mass, vlicl aIIovs llom lo movo frooIy llrougloul coIIs. Organic acids
aIso lavo many vilaI roIos and funclions in pIanls, incIuding conlribul-
ing lo grovll and produclion of fruil, and aro lloroforo appIiod in many
soclors of agricuIluro (AMCA, 2005). Tlo organic acids commonIy found
in foods diffor considorabIy in slrucluro and in lloir inlibilory offocls on
difforonl bacloria (NaIai and Sioborl, 2003).
Various organic acids or organic acid compounds aro usod as addilivos
llal aro diroclIy incorporalod inlo luman food. AIlornalivoIy lloso acids
can bo llo indirocl rosuIl of formonlalion aclivily of slarlor cuIluros oflon
addod lo foods sucl as dairy, vogolabIo, or moal producls. Organic acids
may aIso originalo from rav maloriaIs or bo producod by formonlalion
during procossing and slorago (RicIo, 2003). Ono of llo mosl imporlanl



 
 
phenol:
enol:
ulcohol:
rhIol:
llgure 2.1 GonoraI slrucluro of a fov organic acids.
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 23
lloy aro addod as slabiIizors or prosorvalivos (Gomis, 1992). On llo ollor
land, aIllougl organic acids aro gonoraIIy rocognizod as safo (GRAS) lloy
may aIso produco advorso sonsory clangos (Gomis, 1992, Min ol aI., 2007).
DiIulo soIulions of organic acids (1÷3°) aro, lovovor, gonoraIIy villoul
offocl on llo dosirabIo sonsory proporlios of, for oxampIo, moal vlon usod
as a carcass doconlaminanl (SmuIdors and Groor, 1998, Min ol aI., 2007).
WoaI organic acids lavo an oxlondod lislory as food prosorvalivos
duo lo lloir gonoraI anlimicrobiaI aclivily. Tloy aro, in facl, llo mosl com-
monIy usod clomicaI prosorvalivos of food and aro GRAS, broad-spoc-
lrum, anlimicrobiaI agonls (IIumridgo ol aI., 2004, Sloinor and Sauor, 2003).
Organic acids aro sucl offoclivo food prosorvalivos bocauso, aparl from
lloir anlimicrobiaI inlibilory aclivilios, lloy aIso acl as aciduIanls and in
so doing roduco bacloriaI grovll by Iovoring llo pH of food producls lo
IovoIs llal inlibil bacloriaI grovll (DziozaI, 1990, Hinlon, }r., 2006).
2.2 Siruciurc| !cscripiicn
Organic acids primariIy incIudo llo saluralod slraigll-clain monocarbox-
yIic acids. Dorivalivos of sucl organic acids may consisl of unsaluralod,
lydroxyIic, plonoIic, and muIlicarboxyIic acids. Oflon organic acids aro
aIso roforrod lo as fally acids, voIaliIo fally acids, voaI acids, or carbox-
yIic acids (RicIo, 2003). Organic acids aro nol mombors of a lomoIogous
sorios as lloy diffor in llo numbor of carboxy groups, lydroxy groups,
and carbon÷carbon doubIo bonds in lloir moIocuIos (Hsiao and Sioborl,
lo (1) llo lypo of carbon clain (aIiplalic, aIicycIic, aromalic, and loloro-
cycIic), (2) boing saluralod or nonsaluralod, (3) subslilulod or nonsubsli-
lulod, or (4) llo numbor of funclionaI groups (mono-, di-, lricarboxycIic,
olc.) (Gomis, 1992). Il is, lloroforo, nol lypicaIIy possibIo lo prodicl llo
offocl on food sysloms conlaining moro llan ono acid (Hsiao and Sioborl,
1999). Hovovor, il is Inovn llal lloso slorl-clain voIaliIo organic acids
and quaIily of food (Hsiao and Sioborl, 1999, Yang and Cloong, 2001). Tlo
Iovosl monocarboxyIic (C
1
÷C
4
) aIiplalic acids aro rallor voIaliIo Iiquids
vill a dislincl pungoncy, vloroas lloso acids conlaining moro carbon
aloms aro of a roIalivoIy oiIy subslanco and sIigllIy valor soIubIo.
In comparison, dicarboxyIic acids aro coIorIoss soIids vill moIling
poinls al aboul 100°C. AII lloso acids form somovlal soIubIo molaI saIls
and oslors, of vlicl llo Iallor aro adoqualoIy voIaliIo for gas clromalog-
raply anaIysis. Tloy aIso lavo spoclraI absorplion proporlios llal maIo
llom suilabIo for HIIC anaIysis (Gomis, 1992, Hsiao and Sioborl, 1999).
24 Orgcnic Aci!s cn! Icc! Prcscrtciicn
Tlo slronglls of voaI acids aro moasurod on llo pK
a
scaIo. Tlo pK
a
vaIuo
is llo pH al vlicl llo acid and anion conconlralions aro oquaI (TabIo 2.1).
Tlo smaIIor llo numbor on llis scaIo is, llo slrongor llo acid. In soIu-
lion, voaI acids do nol fuIIy dissocialo inlo ions, bul form oquiIibria
bolvoon unclangod acid moIocuIos and lloir rospoclivo clargod anions
and prolons:
HA A
÷
+ H
+
(acid moIocuIo) (anion) (prolon)
TubIe 2.1 Organic Acids IroquonlIy Assayod in Ioods and
Dissocialion Conslanl
a
MnnncarbnxyIic
Organic acid FornuIa pK
a
Acolic acid CH
3
COOH 4.76
Bonzoic acid C
7
H
6
O
2
4.20
Bulyric acid C
4
H
8
O
2
4.83
Cinnamic acid C
9
H
8
O
2
4.44
Iormic acid CH
2
O
2
3.75
GaIIic acid C
7
H
6
O
5
4.41
Iaclic acid C
3
H
6
O
3
3.83
Iropionic acid C
3
H
6
O
2
4.87
Iyruvic acid C
3
H
4
O
2
2.39
Sorbic acid C
6
H
8
O
2
4.76
DicarbnxyIic
Organic acid FornuIa pK
1
pK
2
Ascorbic acid C
6
H
8
O
6
4.10 11.79
Iumaric acid C
4
H
4
O
4
3.09 4.60
MaIic acid C
4
H
6
O
5
3.46 5.21
Succinic acid C
4
H
6
O
4
4.22 5.70
TricarbnxyIic
Organic acid FornuIa pK
1
pK
2
pK
3
Cilric acid C
6
H
8
O
7
2.79 4.30 5.65
Isocilric acid C
6
H
8
O
7
3.28 4.71 6.39
a
A dissocialion conslanl K
a
is somolimos oxprossod by ils pK
a
, vloro pK
a 10
K
a
. Tloso
pK
a
s aro mainIy usod for covaIonl dissocialions bocauso lloso dissocialion conslanls can
vary groalIy.
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 25
2.3 An ctcrticu c| in!iti!uc| crgcnic
cci!s cn! i|cir cpp|icciicns
2.3.1 Acciic cci!
Acolic acid (Iiguro 2.2) is ono of llo oIdosl clomicaIs Inovn lo luman-
ily and is producod naluraIIy during spoiIago of fruil and corlain ollor
foods by llo prosonco and aclivily of, among ollors, llo acolic acid baclo-
ria (AAB), ono of vlicl is Accic|ccicrium, commonIy found in foodsluffs,
valor, and soiI. Acolic acid is ono of llo main producls of AAB molabo-
Iism (GonzaIoz ol aI., 2005). Tlo acid las GRAS slalus and is approvod
vorIdvido for uso as a food addilivo and prosorvalivo (SmuIdors and
parlicuIarIy in broad ( im oI, on, and TuIumo Iu, 2006).
Acolic acid is Inovn lo bo a slabIo subslanco and is aIso roforrod lo as
¨ollanoic acid¨ or ¨gIaciaI acolic acid¨ (RicIo, 2003). Acolic acid las onIy
ono COOH group, vlicl impIios llal a liglor conconlralion is noodod
llan for an organic acid vill moro llan ono COOH group, lo acliovo llo
samo pH. Il is a voaI acid and cannol dissocialo as compIoloIy as a slrong
acid. A Iovor ionizalion conslanl (K
a
) is claraclorislic of a voaIor acid,
as il yioIds a Iovor amounl of lydrogon ions in soIulion. Tlo ionizalion
amounl of voaI acid in a soIulion musl bo dolorminod from llo ionizalion
conslanl (K
a
). In comparison lo cilric acid vill 3 K
a
(7.447 × 10
÷4
, 1.733 ×
10
÷5
, and 4.018 × 10
÷6
), acolic acid vill 1 K
a
(1.753 × 10
÷5
) is voaIor llan cil-
ric acid (Iormprasorl and Dovalaslin, 2005). Hovovor, acolic acid is moro
inlibilory llan Iaclic acid, bocauso of ils liglor pK
a
vaIuo (IarIas, 1998).
On llo ollor land, acolalo is far Ioss inlibilory lo yoasls llan llo moro
IipopliIic sorbalo (lrans, lrans loxano dionoalo), aIllougl lloy lavo llo
samo pK
a
(4.76). Tlis may bo duo lo llo sorbalo's mucl liglor capacily lo
dissoIvo in mombranos (Bauor ol aI., 2003). In cuIluro modia acolic acid is
O
O
Chemical foimula: CH
3
COOH
llgure 2.2 Slrucluro of acolic acid.
26 Orgcnic Aci!s cn! Icc! Prcscrtciicn
aIso mucl moro inlibilory againsl Iisicric llan Iaclic acid and addilion of
acolic acid usuaIIy rosuIls in groalor coII doslruclion, bul simiIar concon-
lralions of cilric acid and Iaclic acid viII roduco llo pH of a broll sucl as
lryplic soy broll moro llan acolic acid (DoyIo, 1999).
Acolic acid is Iipid soIubIo and abIo lo rapidIy diffuso llrougl llo
pIasma mombrano, a faclor llal las a dramalic offocl on llo pH
i
of a coII
in acids vill slorl aIiplalic clains (sucl as acolic acid), and mucl liglor
conconlralions (20÷80 mM) aro noodod for grovll inlibilion (Hazan,
Iovino, and AboIiovicl, 2004).
2.3.2 Asccr|ic cci!
2.3) and ils saIls lavo, for many docados, boon
Ioading anlioxidanls usod on fruils and vogolabIos in fruil juicos. Tlis
appIicalion mollod is offoclivo in provonling brovning and ollor oxida-
livo roaclions. Ascorbic acid aIso acls as an oxygon scavongor by romov-
ing moIocuIar oxygon in poIyplonoI oxidaso roaclions (Rico ol aI., 2007).
common prosorvalivos in llo produclion of cannod foods (Ioroz-Ruiz,
Marlinoz-Iozano, and Garcia, 2007).
2.3.3 8cnzcic cci!
Bonzoic acid (Iiguro 2.4) is ono of llo oIdosl and mosl commonIy and
vidoIy usod clomicaI prosorvalivos. Hovovor, llo uso of sodium bonzo-
alo as a food prosorvalivo las boon oplimaI in producls llal aro acidic in
O
HO
H
OH
O
HO
HO
Chemical foimula: C
6
H
8
O
6
llgure 2.3
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 2¯
(Barbosa-Cánovas ol aI., 2003), aIllougl il is mainIy associalod vill llo
prosorvalion of fruil and fruil juicos (Sulr and NioIson, 2004). Horo il is
primariIy appIiod as an anlifungaI agonl (Barbosa-Cánovas ol aI., 2003).
Bonzoic acid is aIso oflon usod in combinalion vill sorbic acid in many
lypos of producls. Tlis combinalion is parlicuIarIy popuIar in confoc-
lionory (Sulr and NioIson, 2004). Il las boon doloclod as a naluraI con-
sliluonl of cranborrios, raspborrios, pIums, prunos, cinnamon, and cIovos
(Barbosa-Cánovas ol aI., 2003). In ollor appIicalions, bonzoic acid las aIso
boon usod as a miId anlisoplic in cougl modicinos, moullvaslos, looll-
paslos, and as an anlifungaI in oinlmonls (Oloro-Iosada, 2003). Advorso
offocls of sodium bonzoalo lavo boon roporlod lo bo lyporaclivily and
asllma (IouIlor, 2007).
Dorivalivo bonzoalos and parabonzoalos lavo boon usod primariIy
lorsoradisl, and clooso (Barbosa-Cánovas ol aI., 2003). Ollor foodsluffs
vloro sodium bonzoalo is usod incIudo sofl drinIs, baIod goods, and
IoIIipops (IouIlor, 2007). BonzaIdolydo and bonzoic aIcoloI aro bollor
Inovn lo bo yoasl inlibilors. Bonzoic acid las boon found lo roIoaso fovor
prolons llan suIplilo, nilrilo, or acolic acid and il may bo spocuIalod llal
bonzoic acid is nol a cIassic voaI-acid prosorvalivo. Hovovor, duo lo a
Iovor pK
a
vaIuo, bonzoic acid roIoasos llroo lo four limos moro prolons
llan sorbic acid. Tlis is a sizabIo conconlralion of prolons aIllougl nol
as mucl as ollor voaI-acid prosorvalivos (Slralford and AnsIov, 1998).
Inlibilion of grovll is slrongIy pH-dopondonl and mosl offoclivo undor
acidic condilions. Undor lloso condilions llo prolonalod form of llo acid
is prodominanlIy found (Visli, ViIjaIainon, and IaaIso, 2003). Anollor
unoxpoclod discovory vas llal bonzoic acid appoars lo bo a pro-oxidanl.
Tlis vas unoxpoclod as il is a voII-Inovn facl 2-lydroxybonzoic acid (or
saIicyIic acid) acls as a scavongor of froo radicaIs in titc (Iipor, 1999).
O
OH
Chemical foimula: C
7
H
6
O
2
llgure 2.4 Slrucluro of bonzoic acid.
28 Orgcnic Aci!s cn! Icc! Prcscrtciicn
Bonzoic acid possossos GRAS slalus, and is conjugalod in llo Iivor
lo produco bonzoyIgIycino (or lippuric acid), vlicl is llon oxcrolod in
vloro approprialo amounls of bonzoic acid (or sorbic acid) appoar lo bo
safo as llo acid las boon loslod by Iabs llrougloul llo vorId (Tang and
Wu, 2007). AIllougl sonsory claraclorislics of bonzoic acid aro unInovn,
llo acid couId bo rogardod as a cIassicaI miId pungonl slimuIus. Tlo laslo
of sodium bonzoalo cannol bo doloclod by ono in ovory four of llo popu-
Ialion, bul for lloso vlo can laslo il, il is porcoivod as svool, sour, saIly,
or somolimos billor. Bonzoic acid las aIso boon found lo bo suporior in
bacloricidaI aclivily againsl coIiform and Iaclic acid bacloria in boll llo
slomacl and llo inloslinaI conlonl (Oloro-Iosada, 1999).
2.3.4 Cinncmic cci!
Cinnamic acid (Iiguro 2.5) is a plonoIic compononl (a dorivalivo of plon-
yIaIanino) of sovoraI spicos, incIuding cinnamon (RoIIor, 1995). Il consisls
of a roIalivoIy Iargo famiIy of organic acid isomors oxlraclod from pIanls or
clomicaIIy synllosizod. Cinnamic acid is aIso GRAS and usod as a com-
riaI, anlifungaI, and anliparasilic aclivilios. Hovovor, il las boon found lo
bo parlicuIarIy offoclivo al acidic pH againsl fungi. AIllougl ligl concon-
lralions of cinnamic acid lavo boon roporlod lo causo brovning in somo
fruils (o.g., noclarinos, Iimos, and poars), il las boon found lo bo vory offoc-
livo in proIonging sloIf Iifo of sovoraI imporlanl fruil producls, sucl as
frosl lomalo sIicos slorod al 4°C or 25°C. Tlo }apanoso aro Inovn lo uso
Cinnamic acid is voII Inovn for ils roIo as a plonoIic compound llal
valor or ollanoI and in naluro cinnamic acid dorivalivos aro Inovn lo
O
O
Chemical foimula: C
9
H
8
O
2
llgure 2.5 Slrucluro of cinnamic acid.
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 2º
bo imporlanl molaboIic buiIding bIocIs in llo produclion of Iignins for
lracl irrilanl (RoIIor, 1995).
2.3.5 Ciiric cci!
Cilric acid (Iiguro
uso is slandard in virluaIIy ovory prosorvod food (Marz, 2002). Togollor
vill ils saIls, cilric acid is, in facl, ono of llo mosl commonIy usod
organic acids in llo food as voII as plarmacoulicaI induslrios (Coulo and
Sanroman, 2006). Il aIso las an imporlanl roIo in llo molaI procossing
and clomicaI induslrios (NiIbaIll, Sadrzadol, and Molammadi, 2007).
organic acid prosorvalivos, vlicl vouId bo ¨a IipopliIic, undissocialod
acid llal inlibils microbiaI grovll al Iov pH, by causing inlracoIIuIar
ing grovll of microorganisms by cloIaling divaIonl molaI ions from llo
modium¨ (BruI and Coolo, 1999, Slralford, 1999, NioIson and Arnoborg,
ria (RammoI, 1962, Imai, Banno, and Iijima, 1970, Gralam and Iund, 1986,
NioIson and Arnoborg, 2007).
Cilric acid is a lypicaI producl of formonlalion and vas originaIIy
producod by Iargo formonlalion companios in Woslorn counlrios. Moro
roconlIy llo loclnoIogicaI appIicalions of cilric acid (o.g., in dolorgonls)
lavo conlribulod lo llo produclion and marIoling of moro onvironmon-
laIIy friondIy producls (Marz, 2002). AIllougl cilric acid las a frosl acidic
aIso ils boing liglIy soIubIo, lavo rondorod llo subslanco a dominaling
O
OH
O
HO
O
OH
OH
Chemical foimula: C H
8
O
7
llgure 2.6 Slrucluro of cilric acid.
30 Orgcnic Aci!s cn! Icc! Prcscrtciicn
posilion in llo marIol. Tlo food induslry is llo Iargosl consumor of cilric
acid, oslimalod lo uso aImosl 70° of llo lolaI produclion. Tlis is foIIovod
by llo plarmacoulicaI induslry (aboul 12°) vill various ollor appIica-
lions using llo romaining 18° of llo cilric acid producod (Coulo and
Sanroman, 2006).
Cilric acid las llroo COOH groups and is an lydroxy acid (Iilo ol
aI., 2004). Il conlains lvico as many lydropliIic groups as lydroplo-
al llo surfaco (Iormprasorl and Dovalaslin, 2005). Il is ono of llo Iarg-
osl carboxyIic organic acids producod by Aspcrgi||us nigcr llrougl for-
monlalion of Iov moIocuIar voigll carbolydralo soIulions (NiIbaIll,
Sadrzadol, and Molammadi, 2007). Cilric acid is llo mosl imporlanl
organic acid producod: gIobaI produclion is oslimalod lo bo around
620,000 molric lons por yoar and roprosonls 60° of aII food aciduIanls
uliIizod vorIdvido (KrislnaIumar, 1994, Morosi and Sappino, 1998,
NiIbaIll, Sadrzadol, and Molammadi, 2007). Tlo onliro produclion of
cilric acid is carriod oul by formonlalion. In sludios dono on organic acid
produclion by various yoasl spocios, cilralo vas mosl oflon producod in
llo groalosl amounls by aII llo isoIalos loslod (Guorzoni, Ianciolli, and
Marclolli, 1993). Cilric acid can aIso bo producod by clomicaI synllosis,
aIllougl llo cosl is mucl liglor llan vill formonlalion (Coulo and
Sanroman, 2006).
Dospilo llo popuIarily of cilric acid as a food addilivo and prosorva-
livo, ils slarp and ovorvloIming acidic laslo is, lovovor, incIinod lo ovor-
advanlagos lavo aIso boon nolod vlon using cilric acid as a food addilivo.
Ior oxampIo, duo lo ils lygroscopic naluro, il londs lo caIo vlon usod in
dry povdors sucl as sofl drinI or bovorago mixos. Il aIso las an unovon
dravbacIs, cilric acid is by far llo mosl commonIy usod food aciduIanl.
Tlo iniliaI slarpnoss associalod vill cilric acid is proforabIo in somo ond
Tlo inlibilory offocl of cilric acid on Iisicric mcnccµicgcncs grovll las
boon found lo bo mucl moro ovidonl llan llo inlibilory offocl of ascor-
bic acid. Tlo difforonco in inlibilion bolvoon boll acids is mosl obvious
vlon llo lomporaluro is liglor. Bocauso of llo pK vaIuos of cilric acid
(pK
1
= 3.14, pK
2
= 4.77, and pK
3
= 6.39), il dissocialos slrongIy insido micro-
biaI coIIs (Carrasco, Garcia-Gimono, and SosoIovsIy, 2006).
2.3.6 Icrmic cci!
Iormic acid (Iiguro 2.7) is llo slorlosl clain organic acid (HCOOH). Tlis
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 31
coII and lo accumuIalo vory quicIIy al llo oxponso of llo microbiaI
Dobovoro, 1997, Clavooracl ol aI., 2002). Tlo principaI uso of formic acid
is as a prosorvalivo in IivoslocI food. As sucl il is sprayod on frosl lay or
ollor siIago lo arrosl llo docaying procossos and may aIso causo llo food
lo rolain ils nulrilivo vaIuo Iongor. Il is, lloroforo, vidoIy usod in llo pros-
orvalion of vinlor food for callIo.
A smaII oxcoss of undissocialod formic acid las a slrongor baclori-
cidaI offocl on llo cuIlurabiIily of Ccmpµ|c|ccicr jcjuni and Ccmpµ|c|ccicr
cc|i in comparison vill a Iargo oxcoss of undissocialod propionic or acolic
acid al llo samo pH IovoIs. Il may bo possibIo llal llo slrucluro of lloso
acids is llo mosl imporlanl faclor in llo inlibilion aclivily of C. jcjuni and
C. cc|i viabiIily (Clavooracl ol aI., 2002).
2.3.¯ Iumcric cci!
Iumaric acid (Iiguro 2.8) is ono of llo slrongosl of llo voaI organic acids
usod as a food aciduIanl, primariIy duo lo ils Iov pK
a
vaIuos (3.03 and 4.54),
and is vidoIy found in naluro (Comos and BooIman, 2002). Il is an ossonliaI
parl of pIanl Iifo and aIso llo main by-producl in
by R|izcpus crµzcc,
2005). Iumaric acid is ono of llo cloapor food acids, bul las a Iov soIubiIily
in valor and may aIso lond lo dissoIvo sIovIy. Hovovor, il is somolimos sup-
lo as valor-soIubIo fumaric acid. AIllougl fumaric acid is primariIy addod lo
foodsluffs as an aciduIanl, il aIso las a baclorioslalic funclion (IovIds, 2002).
Iumaric acid vouId llon appoar lo bo a ¨slrongor¨ acid in food and as
IovoI of larlnoss comparod lo ollor food acids. Il is Inovn lo improvo llo
quaIily of food and bovoragos and may aIso roduco llo cosl of sucl prod-
ucls. Iumaric acid may aIso bo usod in animaI food. Sinco 1946 fumaric
O
O
H
Chemical foimula: CH
2
O
2
llgure 2.7 Slrucluro of formic acid.
32 Orgcnic Aci!s cn! Icc! Prcscrtciicn
acid las boon usod in food and bovorago producls and il is sliII usod in
vloal and corn lorliIIas, sour dougl and ryo broads, biscuil dougl, fruil
roIalivoIy slrong acid laslo and Iov soIubiIily lavo mado il Ioss dosir-
abIo for corlain food appIicalions. Tlo uso of fumaric acid las, lloroforo,
docIinod sinco llo 1980s, vlon in 1985 noarIy 50 miIIion pounds voro con-
sumod. Nov fumaric acid las lo compolo vill ollor aciduIanls sucl as
cilric acid, larlaric acid, and maIic acid, aIllougl il is Ioss oxponsivo llan
somo of lloso subslilulos (IovIds, 2002).
2.3.8 G|uccnic cci!
GIuconic acid (Iiguro 2.9) is a miId organic acid dorivod from gIucoso by
a simpIo oxidalion roaclion, faciIilalod by llo onzymo gIucoso oxidaso
in fungi and gIucoso dolydrogonaso in bacloria (sucl as G|uccnc|ccicr).
MicrobiaI produclion of gIuconic acid dalos bacI sovoraI docados and las
O
OH
HO
OH OH
OH
OH
Chemical foimula: C
6
H
12
O
7
llgure 2.9
O
OH
O
HO
Chemical foimula: C
4
H
4
O
4
llgure 2.8 Slrucluro of fumaric acid.
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 33
sinco boon llo proforrod mollod for produclion. Aspcrgi||us nigcr, in par-
licuIar, is mosl vidoIy usod in llo formonlalion procoss. GIuconic acid and
ils dorivalivos (sucl as sodium gIuconalo) aro vidoIy appIiod in llo food
and plarmacoulicaI induslrios. Aparl from boing a miId organic acid, gIu-
conic acid is aIso noncorrosivo, nonvoIaliIo, and nonloxic. Il is popuIar for
causing a rofrosling sour laslo in various foodsluffs, incIuding vino and
fruil juicos and is usod for provonlion of miIIslono in llo dairy induslry.
Tlo dorivalivo gIucono- -Iaclono funclions as a sIov-acling aciduIanl in
procossing moal sucl as sausago, vloroas sodium gIuconalo is Inovn lo
bo liglIy ovorpovoring (Ramanclandran ol aI., 2006).
2.3.º Icciic cci!
Iaclic acid (Iiguro 2.10) is an organic acid vill a vido rango of indus-
lriaI appIicalions. Il is aIso an lydroxyacid (2-lydroxypropionic,
CH
3
agonl, and of courso as a prosorvalivo (VaIIi ol aI., 2006). AIllougl Iaclic
acid aIso las vido appIicalions in llo plarmacoulicaI, Ioallor, and lox-
liIo induslrios and as a clomicaI foodslocI (Coulo and Sanroman, 2006),
a roviov pubIislod in 1995 roporlod llal in llo Unilod Slalos 85° of llo
Iaclic acid vas usod in food or food-roIalod appIicalions (Zlang, }in, and
KoIIy, 2007). Iaclic acid is nol naluraIIy prosonl in foods, bul is producod
during formonlalion of foods by Iaclic acid bacloria. Tloso foods incIudo
sauorIraul, picIIos, oIivos, and somo moals and cloosos (Barbosa-Cánovas
lo aroma and prosorvalion (Do Ia ol aI., 2005).
O
OH
OH
Chemical foimula: C
3
H
6
O
3
llgure 2.10
34 Orgcnic Aci!s cn! Icc! Prcscrtciicn
and KoIIy, 2007). Tlis is llo form usod by llo luman molaboIism and llo
onzymo
mucl moro inlibilory for |. cc|i I.
mcnccµicgcncs
and
i
of I. mcnccµicgcncs as
voII as |. cc|i (McWiIIiam Ioilcl and Slovarl, 2002). Iaclic acid ponolra-
lion across llo coII mombrano appoars lo bo simiIar for llo lvo isomors.
An addilionaI anlimicrobiaI moclanism las boon doscribod for Iaclic
aI., 2004). |. cc|i and I. !c||rucc|ii subsp. |u|gcricus
(Bonllin and ViIIadson, 1995, Buncl ol aI., 1997), vloroas I. mcnccµicgcncs
llal lloy inlrinsicaIIy produco. Tlis impIios an addilionaI rosislanco
Iaclic acid is a major ond producl from formonlalion of a carbolydralo
by Iaclic acid bacloria (Tormo and Izco, 2004). Hovovor, Iaclic acid can
bo producod commorciaIIy by oillor clomicaI synllosis or formonlalion.
Tlo clomicaI synllosis rosuIls in a racomic mixluro of llo lvo isomors
vloroas during formonlalion an oplicaIIy puro form of Iaclic acid is pro-
ducod. Hovovor, llis may dopond on llo microorganisms, formonlalion
subslralos, and formonlalion condilions. Iaclic acid can bo producod from
ronovabIo maloriaIs by various spocios of llo fungus R|izcpus. Tlis las
many advanlagos as opposod lo bacloriaI produclion bocauso of amyIoIylic
claraclorislics, Iov nulrionl roquiromonls, and llo fungaI biomass, vlicl
is a vaIuabIo formonlalion by-producl (Zlan, }in, and KoIIy, 2007).
Sodium Iaclalo is llo sodium saIl of naluraI Iaclic acid (
compononl of muscIo lissuo (Cloi and Clin, 2003). Il is primariIy usod in moal
producls lo oxlond coId slorago and llo offocls aro moro baclorioslalic llan
bacloricidaI (BoIlon ol aI., 2002). Sodium Iaclalo is aIso producod by microbiaI
formonlalion and las boon usod lo conlroI microbiaI grovll during slorago,
Clin, 2003). Tlo spoclrum of aclivily of sodium Iaclalo is acluaIIy quilo nar-
aI., 2002). Il aIso las an anlibacloriaI offocl on pallogons sucl as C|csiri!ium
|ciu|inum and I. mcnccµicgcncs, llo Iallor boing nolorious for causing sovoro
condilions, llo inlibilory aclivily of Iaclic acid againsl I. mcnccµicgcncs can
bo oillor bacloriocidic or baclorioslalic (Gravoson ol aI., 2004).
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 35
I. mcnccµicgcncs can uliIizo Iaclalo as a carbolydralo sourco (Kouassi
nol roaIIy appIicabIo lo I. mcnccµicgcncs. Tlis aIso suggosls considorabIo
spocios-lo-spocios varialion in roIalivo sonsilivily lo llo lvo isomors, vlicl
CIoaror insigll inlo llo moclanisms invoIvod couId onlanco llo oplimaI
uso of Iaclic acid or Iaclic acid producors (Gravoson ol aI., 2004).
Iaclic acid is commonIy found, vlicl conlribulos lo ils vido uso in
food and food-roIalod induslrios. Il aIso las llo polonliaI for produclion
of biodogradabIo and biocompalibIo poIymors. Tloso producls lavo boon
provon lo bo onvironmonlaIIy friondIy aIlornalivos lo biodogradabIo pIas-
lics dorivod from polroclomicaI maloriaIs (Zlang, }in, and KoIIy, 2007).
Iaclic acid is sIigllIy Iipid soIubIo and diffusos sIovIy llrougl llo coII
mombrano. As a rosuIl of llis, llo disruplion of llo coII pH
i
is nol ils main
modo of inlibilion (Gravoson ol aI., 2004).
Iaclic acid is llo major IAB molaboIilo, causing pH roduclions llal
inlibil many microorganisms. Hovovor, boll acolic and propionic acids
lavo liglor pK
a
vaIuos llan Iaclic acid and, lloroforo, lavo a liglor pro-
porlion of undissocialod acid al a corlain pH (Sclnuror and Magnusson,
2005).
2.3.10 Mc|ic cci!
MaIic acid (Iiguro 2.11) is an aIpla lydroxy organic acid, vidoIy found in
appIos and ollor fruils and is, lloroforo, somolimos roforrod lo as a fruil
maIs, incIuding lumans. MaIic acid is aIso Inovn as lydroxybulanooic
acid or lydroxysuccinic acid. Il is a cliraI moIocuIo, llo naluraIIy occurring
O
OH
HO
O
OH
Chemical foimula: C
4
H
6
O
5
llgure 2.11 Slrucluro of maIic acid.
36 Orgcnic Aci!s cn! Icc! Prcscrtciicn
ono. MaIic acid is aIso vidoIy found in vogolabIos and is a polonl inlibilor
of llo grovll of yoasls and somo bacloria (Barbosa-Cánovas ol aI., 2003).
MaIic acid is moro offoclivo llan acolic acid and Iaclic acid in inlibiling
grovll of llormopliIic bacloria, bul is nol as offoclivo as Iaclic acid in
supprossing grovll of I. mcnccµicgcncs (DoyIo, 1999).
MaIic acid las a smooll Iingoring laslo. AIllougl il aIso las a larl
laslo, llis is nol as slarp as llal of cilric acid, yol il is Iongor Iasling. Il las
aIso boon found lo masI llo billor aflorlaslo of synllolic svoolonors, yol
vlon using svoolonors sucl as asparlamo, il vas found llal llo sIovor
incroaso lo poaI larlnoss doos nol ovorpovor llo svoolonors and as sucl,
Ioss svoolonor is noodod. Hovovor, in somo ond producls sucl as cilrus-
abIo (IovIds, 2002).
Walor usod in many manufacluring procossos oflon conlains smaII
amounls of lard valor saIls. Hovovor, maIic acid is liglIy soIubIo, and
llo soIubiIily of ils caIcium saIl provonls cIoudinoss of ond producls
conlaining maIic acid as an aciduIanl. MaIic acid and ils saIls lavo boon
aciduIanl as voII as a pH conlroI agonl al IovoIs varying from 6.9° for
lard candy lo 0.7° for miscoIIanoous usos (IovIds, 2002).
2.3.11 Prcpicnic cci!
Iropionic acid (Iiguro
acid occurs in foods by naluraI procossing. Il las boon found in Sviss
clooso al conconlralions of up lo 1° and is producod by llo baclorium
Prcpicni|ccicrium s|crmcnii. AnlimicrobiaI aclivily of propionic acid is
roporlod lo bo primariIy againsl moIds and bacloria (Barbosa-Cánovas
ol aI., 2003). CommorciaI producls conlaining propionic acid incIudo
OH
O
Chemical foimula: C
3
H
6
O
2
llgure 2.12 Slrucluro of propionic acid.
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 3¯
Microguard
® ®
, vloro llo uso of a Prcpicni|ccicrium |rcu!cn-
rcic|ii slrain, aIong vill Iccic|cci||us r|cmncsus incroasos inlibilory acliv-
ily againsl fungi and somo Gram-posilivo bacloria (CapIico and IilzgoraId,
1999). Tlo oslors of propionic acid lavo fruilIiIo odors and aro somolimos
an inlormodialo in llo produclion of ollor clomicaIs sucl as poIymors.
CoIIuIoso acolalo propionalo is a usofuI llormopIaslic, and vinyI propi-
onalo is usod, in moro spociaIizod appIicalions, lo maIo poslicidos and
plarmacoulicaIs (Sclnuror and Magnusson, 2005).
Iropionic acid is offoclivo al roducing fungaI grovll, ospociaIIy al
Iovor pH, by affocling fungaI mombranos al pH vaIuos boIov 4.5. SimiIar
lo acolic acid, propionic acid aIso inlibils amino acid uplaIo. Tlo saIls of
propionic acid, sucl as sodium propionalo and ammonium propionalo
(Sclnuror and Magnusson, 2005).
2.3.12 Scr|ic cci!
Sorbic acid (Iiguro 2.13) is llo voaI organic acid mosl oxlonsivoIy usod
in food prosorvalion. Il las GRAS slalus and il is usod in any food, ani-
maI food, or plarmacoulicaI nooding prosorvalion (Iipor, 1999). Togollor
vill llo organic acids, bonzoic acid and acolic acid, sorbic acids (or ircns-
ircns-2,4-loxadionoic acids) aro llo mosl commonIy usod clomicaI pro-
sorvalivos of food and aro GRAS, broad-spoclrum, anlimicrobiaI agonls
(IIumridgo ol aI., 2004). Sorbic acid is aIso oflon usod in combinalion vill
bonzoic acid for various lypos of producls and confoclionory (Sulr and
NioIson, 2004).
Sorbic acid is proforrod lo ollor organic acids bocauso of ils plysioIogi-
caI larmIossnoss and organoIoplic noulraIily. In llo Unilod Slalos, sorbic
acid is a GRAS subslanco and ils uso is pormillod in any food producl
lo vlicl prosorvalivos may bo addod (Banorjoo and SarIar, 2004). Sorbic
O
OH
Chemical foimula: C
6
H
8
O
2
llgure 2.13 Slrucluro of sorbic acid.
38 Orgcnic Aci!s cn! Icc! Prcscrtciicn
acid is a six-carbon monocarboxyIic acid, unsaluralod al posilions 2 and 4,
Inovn lo bo a mombrano-aclivo compound (Slralford and AnsIov, 1998).
Sorbic acid and ils saIls lavo sovoraI advanlagos as food prosorvalivos.
Tloy aro liglIy aclivo againsl fungi as voII as a vido rango of bacloria, in
parlicuIar llo calaIaso-posilivo organisms, lloir offoclivo conconlralions
normaIIy do nol aIlor llo laslo or odor of a food producl, and lloy aro aIso
considorod larmIoss. Hovovor, polassium saIl is moro commonIy usod
bocauso of ils slabIo naluro. Iolassium sorbalo is aIso mucl moro soIubIo
and vory suilabIo for uso in dipping and spraying doconlaminalion prac-
licos (GonzaIoz-Iandos and Dominguoz, 2007). SoIubiIily is 58.2° (139
g/100 mI) al 20°C. Il may aIso bo usod for spraying or moloring fruil and
vogolabIo producls. Tlo inlibilory aclivily of sorbalos is simiIar lo sorbic
acid, bul usuaIIy 25° moro polassium sorbalo is noodod lo lavo llo samo
offocl. Hovovor, sorbalos lavo many usos bocauso of lloir miIdor laslo,
groalor offoclivonoss, and broador pH rango (up lo 6.5), vlon comparod lo
oillor bonzoalo or propionalo. Tlis vouId offoclivoIy moan llal in foods
vill a vory Iov pH, sorbalo IovoIs as Iov as 200 ppm may givo moro llan
adoqualo proloclion. Sorbalo can, lloroforo, bo appIiod lo a vido rango of
food producls and bovoragos, incIuding among ollors, syrups, fruil juicos,
vinos, joIIios, jams, saIads, and picIIos (Barbosa-Cánovas ol aI., 2003). Tlo
liglor soIubiIily of polassium sorbalo, lloroforo, rondors il llo proforrod
form of sorbic acid as a prosorvalivo in foods. Hovovor, sorbic acid is moro
soIubIo in oiIs llan llo polassium saIl. Sorbic acid and polassium sorbalo
aro nol vory offoclivo al conlroIIing spoiIago in baIory producls, vloro
llo pH may oxcood pH 7. Iolassium sorbalo may onIy bo usofuI al pH 6
bul nol al pH 7.5 (Marín ol aI., 2003).
Sorbic acid las a pK
a
vaIuo of 4.76 and in a pH 4.2 soIulion aboul
75° viII bo in ils undissocialod form. Al pH 7 > 1° viII bo undissoci-
alod. AIllougl acolic acid las llo samo pK
a
vaIuo as sorbic acid, a lonfoId
liglor conconlralion of acolic acid is roquirod lo produco llo samo oxlonl
of grovll inlibilion as sorbic acid (Iapadimilriou ol aI., 2007).
UnliI roconlIy, llo uso of sorbic acid vas a slandard approacl for pros-
orvalion in llo food induslry. Hovovor, mucl allonlion las nov focusod
on llo dovoIopmonl of rosislanco againsl llis voaI organic acid prosorva-
livo (BruI ol aI., 2002).
As bonzoic acid is gonoraIIy assumod lo bo safo bocauso il is conju-
galod in llo Iivor lo produco bonzoyIgIycino (lippuric acid), sorbalo is aIso
IargoIy oxcrolod in llis caso as llo oxidalion producl 2,4-loxadionodioxic
acid (Iipor, 1999). Sorbalo las boon found lo lavo a baclorioslalic offocl on
I. mcnccµicgcncs,
I. mcnccµicgcncs may bo duo lo varialions in modia or food, pH, or sorbalo
conconlralions (GonzaIoz-Iandos and Dominguoz, 2007). Iolassium sor-
balo las boon found lo bo mucl Ioss offoclivo llan sorbic acid al inlibiling
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 3º
Marín ol aI., 2003), vloroas sorbic acid is Ioss IinIod lo pH (Sllonborg and
Ignal'ov, 1970).
2.3.13 Succinic cci!
Succinic acid (aIso caIIod bulanodoic acid) (Iiguro 2.14) is a dicarboxyIic
acid of four carbon aloms and occurs naluraIIy in pIanl and animaI lis-
cycIo) in llo body. Succinic acid is a coIorIoss cryslaIIino soIid modium
vill a saIly billor laslo. Il is soIubIo in valor, sIigllIy soIubIo in ollanoI,
lolraclIorido, and oiI ollor (ClomicaIIand21.com, 2008). Succinic acid is
usod in foods as a soquoslranl, buffor, and noulraIizing agonl. Il is aIso
usod as a clomicaI inlormodialo in modicino, and in llo manufacluring of
Iacquors and porfumo oslors (Hcu|cµ, 1988).
2.3.14 1cricric cci!
Tarlaric acid (Iiguro 2.15) is aIso ono of llo lydroxy acids (Iilo ol aI.,
2004). Il is naluraIIy prosonl in fruils sucl as pinoappIos and grapos and
is consoquonlIy aIso llo major acid in vino and vino vinogars (Barbosa-
Cánovas ol aI., 2003, MoraIos, GonzaIoz, and Troncoso, 1998). IrimariIy
duo lo ils Iov pK
a
vaIuos (3.03 and 4.54), larlaric acid is oflon usod as
acid is smoollor llan llal of cilric acid and il las a liglor poaI acid
laslo llan cilric acid and llis is aIso Iongor Iasling. Tarlaric acid may
voII bo llo mosl oxponsivo among llo acids commonIy usod in food
(IovIds, 2002).
O
OH
O
HO
Chemical foimula: C
4
H
6
O
4
llgure 2.14 Slrucluro of succinic acid.
40 Orgcnic Aci!s cn! Icc! Prcscrtciicn
2.3.15 Oi|cr cci!s
IlonyIIaclic acid (Iiguro 2.16) is anollor organic acid vill an inlorosling
polonliaI for appIicalion as an anlimicrobiaI agonl in food. Il las a broad
Conconlralions roquirod for anlifungaI aclivily, parlicuIarIy againsl moIds
from baIory producls aro gonoraIIy Iovor llan conconlralions roquirod
againsl bacloriaI food conlaminanls. IlonyIIaclic soIulions aro odorIoss
(Iavormicocca, VaIorio, and Visconli, 2003).
GaIIic acid (aIso caIIod 3,4,5-lrilydroxybonzoic acid) (Iiguro 2.17) is a
naluraI pIanl plonoI. Il is an organic acid found in vaInuls, sumac, vilcl
lazoI, loa Ioavos, oaI barI, and ollor pIanls. GaIIic acid las boon found lo
O
O
O
H
H
Chemical foimula: C
9
H
10
O
3
llgure 2.16 Slrucluro of plonyIIaclic acid.
O
OH
O
HO
OH
OH
Chemical foimula: C
4
H
6
O
6
llgure 2.15 Slrucluro of larlaric acid.
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 41
possoss anlifungaI and anliviraI proporlios, and dorivalivos sucl as propyI
gaIIalo, oclyI gaIIalo, IauryI gaIIalo, and dodocyI gaIIalo aro aIso vidoIy
usod as food addilivos in roducing rancidily and as prosorvalivos (Van dor
Hoijdon, }ansson, and SlriI, 1986, Sorrano ol aI., 1998, Nilo ol aI., 2001).
2.4 Gcncrc| cpp|icciicns
Organic acids, inorganic anions, amino acids, and carbolydralos aro
plarmacoulicaIs, agricuIluro, and food scionco (Cai ol aI., 1999). Organic
acids lavo lradilionaIIy boon appIiod lo a vido varioly of foods and aro
curronlIy llo mosl commonIy usod food prosorvalivos (GouId and }onos,
1989, Won, Wang, and Iong, 2007). Tloso compounds and lloir saIl doriva-
livos lavo for many docados boon usod lo offoclivoIy conlroI llo grovll of
soIocl microorganisms by Iovoring llo pH of foods. Tloy aro addod doIib-
oraloIy lo food producls or can bo funclionaI as by-producls as a rosuIl
of formonlalion lo acidify llo food lo conlroI microbiaI conlaminalion
and moro imporlanl, foodborno pallogons (Murply ol aI., 2006). Organic
moal producls (BoIlon ol aI., 2002). Somo organic acids, sucl as ascorbic
acid and cilric acids aro mosl gonoraIIy usod as prosorvalivos for cannod
foods or ovon frosl saIad vogolabIos (Ioroz-Ruiz, Marlinoz-Iozano, and
Garcia, 2007, Rico ol aI., 2007). SaIls of organic acids aro usod oxlonsivoIy
in moal and pouIlry producls lo onlanco microbioIogicaI safoly of lloso
producls by conlroIIing pallogons sucl as Iisicric mcnccµicgcncs. In pro-
cossod moal, bufforod saIls, aIono or in combinalion, aro usod as ingrodi-
onls lo provido an addilionaI moasuro of safoly during cliIIing (}unoja
and Tlipparoddi, 2004).
Somo organic acids, sucl as sorbic acid and bonzoic acid, aro vidoIy
rogardod as llo mosl aclivo againsl yoasls and moIds, and nol againsl
OH
O
OH
OH HO
Chemical foimula: C
7
H
6
O
5
llgure 2.17 Slrucluro of gaIIic acid.
42 Orgcnic Aci!s cn! Icc! Prcscrtciicn
bacloria as sucl (GonzaIoz ol aI., 1998). In llo animaI food induslry, organic
(RicIo, 2003). Organic acids aro aIso llo mosl commonIy uliIizod anlimi-
crobiaI agonls in odibIo coalings (Durango, Soaros, and Andrado, 2006).
Irosorvalion of baIory producls commonIy invoIvos llo uso of prosorva-
livos sucl as propionalos and sorbalos, and somolimos bonzoalos (Marín
ol aI., 2003). Sodium bonzoalo is usod in sofl drinIs, baIod goods, and
IoIIipops (IouIlor, 2007).
macoulicaIs, modicino, and llo produclion of ollor clomicaIs. Ior oxam-
pIo, cinnamic acid is synllosizod on a commorciaI scaIo from slyrono and
carbon lolraclIorido (RoIIor, 1995). Duo lo biodogradabIo proporlios, lloro
is a groving domand for organic acids for llo produclion of poIymoric
maloriaIs (BaiIIy, 2002).
2.5 Icc! prc!ucis nciurc||µ
ccnicining crgcnic cci!s
Organic acids occur naluraIIy in many foods as a rosuIl of molaboIic pro-
cossos, lydroIysis, or bacloriaI grovll (TabIo 2.2). AIlornalivoIy lloy can
2.5.1 Iruii
Various organic acids aro commonIy found lo bo naluraI consliluonls of
fruil. Cilric acid can bo found in aImosl aII fruils, ospociaIIy cilrus fruil and
pinoappIo (NiIbaIll, Sadrzadol, and Molammadi, 2007). MaIic acid is aIso
TubIe 2.2 Organic Acids NaluraIIy Iound in Ioodsluffs
Organic acid Foodstuff
Acolic acid Vinogar
Bonzoic acid Cranborrios, prunos, groongago pIums, cinnamon, ripo
cIovos, appIos
Bulyric acid Bullor
Cilric acid Cilrus fruils (orangos, Iomons, grapofruil),
bIacIcurronls, slravborrios
Iormic acid Cilrus ossonliaI oiIs
GaIIic acid Wilcl lazoI, gaIInuls, loa Ioavos
Iaclic acid Sour miII producls (yogurl, collago clooso)
MaIic acid AppIos, clorrios, pIums
OxaIic acid Tomaloos
Tarlaric acid Grapo juicos
C|cpicr iuc. Nciurc cn! ccmpcsiiicn c| crgcnic cci!s 43
vidoIy found in fruils and vogolabIos (Barbosa-Cánovas ol aI., 2003). Bonzoic
acid is a common plonoIic in cranborrios, ospociaIIy in froslIy squoozod
cranborry juico. Il is considorod lo bo llo main anlifungaI agonl in cranbor-
rios (Ionnoy ol aI., 2004). Bonzoic acid is aIso llo naluraI consliluonl of rasp-
borrios, pIums, prunos, Iingonborrios, cIoudborrios, cinnamon, and cIovos
(Barbosa-Cánovas ol aI., 2003, Bo-Onisli ol aI., 2004). Tlo bonzoic concon-
lralion is ospociaIIy ligl in Iingonborrios (0.6÷1.3 g/I froo bonzoic acid) and
llo pH Iov (pH 2.6÷2.9). Conconlralion of bonzoic acid is incroasod furllor
if llo fruil or fruil juico is slorod in varm condilions (Bo-Onisli ol aI., 2004).
Tarlaric acid is commonIy found in pinoappIos, grapos, and grapo-dorivod
producls. Il is, lloroforo, aIso prosonl in roIalivoIy Iargo amounls in vino
vinogar, incIuding baIsamic vinogar, and in Iov conconlralion in cidor vin-
ogars (MoraIos, GonzaIoz, and Troncoso, 1998).
Organic acids lavo boon doscribod as funclioning as slrong anlimi-
crobiaI agonls againsl psyclroplyIic and mosopliIic microorganisms in
frosl-cul fruils as voII as vogolabIos. Ascorbic acid and -carolono aro
anlioxidanls aIso prosonl in llo groalosl quanlilios in fruils and vogolabIos,
bul aro bollor Inovn for lloir oxidalivo claraclorislics (Rico ol aI., 2007).
2.5.2 juiccs
Iruil juicos proparod from llo puIp conlain roIalivoIy Iargo amounls of
cilric acid (HayaIava, IinIo, and IinIo, 1999). In mosl juicos cilralo is
omniprosonl, and maIic acid is prosonl in ligl conconlralions, vill min-
ulo conconlralions of ollor organic acids sucl as Iaclic acid (AroIIano ol
cilric acid (VaIoro ol aI., 2000).
2.5.3 Winc cn! tincgcr
Acolic acid is llo major voIaliIo acid in vino. Al IovoIs abovo 1.2÷1.4 g/I,
il is Inovn lo bo ono of llo main roasons for vino spoiIago (GonzaIoz ol
aI., 2005). Acolic acid is aIso an aclivo ingrodionl in lousoloId vinogar,
and common vlilo lousoloId vinogar consisls of approximaloIy 5° aco-
lic acid (Korll and Bradon, 2007). Il is spocuIalod llal acidily, aIcoloI con-
and rovoralroI may bo rosponsibIo for anlimicrobiaI aclivilios roporlod for
vino againsl foodborno pallogons. Tlis las roconlIy ovoIod mucl inlor-
osl and llo quoslion arisos vlollor vino formuIalions can bo dovisod and
appIiod in improving food safoly. Tloso vino subslancos vouId llon bo
rogardod as nonloxic, food-compalibIo, and pIanl-dorivod anlimicrobiaIs
(Iriodman ol aI., 2006).
44 Orgcnic Aci!s cn! Icc! Prcscrtciicn
2.5.4 Dcirµ
Cilric acid is an organic acid found in abundanco in rav miII, vloroas
Iaclic acid is found lo bo moro provaIonl in yogurl and clooso (Tormo and
Izco, 2004).
2.5.5 Cc||cc
MaIic and cilric acids aro aIroady prosonl in llo groon coffoo boan, bul
mosl of llo acidily in llo coffoo boan is gonoralod al llo boginning of llo
roasling procoss (Rodriguos ol aI., 2007).
2.5.6 8c|crµ prc!ucis
Sourdougl las Iong boon Inovn lo improvo llo sloIf Iifo of broad and
baIory producls, primariIy bocauso of llo oxislonco of Iaclic acid pro-
ducod by Iaclic acid bacloria (Iavormicocca, VaIorio, and Visconli, 2003).
2.5.¯ Hcncµ
Tlo naluraI occurronco of varying amounls of organic acids in lonoys
from difforonl goograplicaI aroas lavo boon documonlod. Mucl rosoarcl
is boing dono lo dolormino llo uso of lonoy as an anlimicrobiaI agonl in
various food sysloms (Suaroz-Iuquo ol aI., 2002).
Rc|crcnccs
AMCA (Agrobosl MuIli CloIalon Advanlago). 2005. Agrobosl, AuslraIia (ITY),
Ild. lllp://vvv.agrobosl.com.au/amca.pdf.
AroIIano, M., Andrianary, }., Dodiou, I., Coudorc, I., and Iuig, I. 1997. Mollod
dovoIopmonl and vaIidalion for llo simuIlanoous dolorminalion of
organic and inorganic acids by capiIIary zono oIoclroplorosis. jcurnc| c|
C|rcmcicgrcp|µ A 765:321÷328.
BaiIIy, M. 2002. Iroduclion of organic acids by bipoIar oIoclrodiaIysis: RoaIizalions
and porspoclivos. Dcsc|inciicn 144:157÷162.
Banorjoo, M. and SarIar, I.K. 2004. Anlibiolic rosislanco and suscoplibiIily lo somo
food prosorvalivo moasuros of spoiIago and pallogonic microorganisms
from spicos. Icc! Micrc|ic|cgµ 21:335÷342.
Barbosa-Cánovas, G.V., Iornándoz-MoIina, }.}., AIzamora, S.M., Tapia, M.S., Iópoz-
MaIo, A., and Clanos, }.W. 2003. GonoraI considoralions for prosorvalion of
fruils and vogolabIos. In: Hcn!|ing cn! Prcscrtciicn c| Iruiis cn! Vcgcic||cs |µ
Ccm|inc! Mci|c!s |cr Rurc| Arccs. Romo: Iood and ArgricuIluro Organizalion
of llo Unilod Nalions.