Results for:
PubChem ID: 689043

(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic Acid

Mass-Spectra

Compound Details

Synonymous names
caffeic acid
3,4-Dihydroxycinnamic acid
331-39-5
trans-caffeic acid
501-16-6
3-(3,4-dihydroxyphenyl)acrylic acid
3,4-Dihydroxybenzeneacrylic acid
(E)-3-(3,4-dihydroxyphenyl)acrylic acid
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
3-(3,4-Dihydroxyphenyl)-2-propenoic acid
(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Caffeicacid
Cinnamic acid, 3,4-dihydroxy-
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-
4-(2-Carboxyethenyl)-1,2-dihydroxybenzene
trans-Caffeate
CCRIS 847
NSC 57197
3,4-Dihydroxy-trans-cinnamate
3-(3,4-Dihydroxyphenyl)propenoic acid
(E)-3,4-dihydroxycinnamic acid
HSDB 7088
UNII-U2S3A33KVM
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (E)-
71693-97-5
EINECS 206-361-2
U2S3A33KVM
NSC-57197
Caffeate
NSC-623438
CHEBI:16433
AI3-63211
trans-3,4-Dihydroxycinnamic Acid
3-(3,4-Dihydroxy phenyl)-2-propenoic acid
NSC57197
331-89-5
CHEMBL145
3-(3,4-dihydroxyphenyl)prop-2-enoic acid
MLS000069738
CHEBI:36281
MFCD00004392
NSC623438
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (2E)-
SMR000058214
(2E)-3-(3,4-dihydroxyphenyl)acrylic acid
CAFFEIC ACID (IARC)
CAFFEIC ACID [IARC]
Caffeic acid - Natural
SR-01000000203
caffeic acid, (E)-isomer
DTXSID5020231
caffeic-acid
Caffeic acid pure
Caffeic acid, 1
Caffeic acid 1000 microg/mL in Acetone
3,4-dihydroxycinnamic acid (caffeic acid)
Caffeic Acid,(S)
Caffeic Acid1507
Caffeic acid, trans-
3,4-dihydroxycinnamate
CAFFEIC ACID natural
Opera_ID_1700
CAFFEIC ACID [MI]
CAFFEIC ACID [DSC]
Cinnamic acid,4-dihydroxy-
3,4-Dihydroxycinnamic acid, predominantly trans
CAFFEIC ACID [HSDB]
CAFFEIC ACID [INCI]
3,4-Dihydroxybenzeneacrylate
SCHEMBL23358
MLS001076493
MLS002207132
MLS002222302
MLS006011849
BIDD:ER0456
DTXCID10231
SPECTRUM1503987
CAFFEIC ACID [WHO-DD]
2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, (2E)-
3,4-Dihydroxycinnamate, XVII
BDBM4375
cid_689043
GTPL5155
AMY3943
Trans 3,4-Dihydroxycinnamic acid
DTXSID901316055
HMS2235G09
HMS3260J17
HMS3649O17
BCP28271
HY-N0172
Tox21_200648
Tox21_500208
BBL012113
Caffeic Acid - CAS 331-39-5
CCG-38895
s2277
STK397812
Caffeic acid, >=98.0% (HPLC)
2-Propenoic acid,4-dihydroxyphenyl)-
AKOS000144463
AC-8006
CS-8205
DB01880
LP00208
SDCCGMLS-0002982.P003
SDCCGSBI-0050196.P004
NCGC00017364-04
NCGC00017364-05
NCGC00017364-06
NCGC00017364-07
NCGC00017364-08
NCGC00017364-09
NCGC00017364-10
NCGC00017364-11
NCGC00017364-12
NCGC00017364-13
NCGC00017364-22
NCGC00022654-03
NCGC00022654-04
NCGC00022654-05
NCGC00022654-06
NCGC00022654-07
NCGC00022654-08
NCGC00022654-09
NCGC00258202-01
NCGC00260893-01
NCGC00263641-01
(E)-3-(3,4-dihydroxyphenyl)acrylicacid
AS-10895
BP-30112
CAS-331-39-5
SMR004703501
XC164210
4-(2'Carboxyvinyl)-1,2-dihydroxybenzene
Caffeic acid, purum, >=95.0% (HPLC)
DB-318886
DB-321780
HY-121231
AB00490047
CS-0081280
EU-0100208
NS00010313
SW197202-3
2-Morpholin-4-yl-isonicotinicacidhydrochloride
2-Propenoic acid, 3-(3,4-dihdroxyphenyl)-
(E)-3-(3,4-dihydroxyphenyl)prop-2-enoicacid
C 0625
C-1500
C01197
C01481
EN300-1067793
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid
A851723
CAFFEIC ACID (CONSTITUENT OF BLACK COHOSH)
Q414116
SR-01000000203-2
SR-01000000203-6
SR-01000000203-7
SR-01000000203-8
BRD-K09900591-001-06-9
SR-01000000203-13
CAFFEIC ACID (CONSTITUENT OF BLACK COHOSH) [DSC]
F3096-1708
Z240113804
2',3-DIHYDROXY-4,4',6'-TRIMETHOXYCHALCONE_met021
2',4-DIHYDROXY-3,4',6'-TRIMETHOXYCHALCONE_met023
8B3E4DA7-F3B0-4972-A315-2E387071737F
trans-Caffeic acid, certified reference material, TraceCERT(R)
Caffeic acid, matrix substance for MALDI-MS, >=99.0% (HPLC)
Caffeic acid, United States Pharmacopeia (USP) Reference Standard
Caffeic acid, matrix substance for MALDI-MS, >=99.0% (HPLC), powder, light beige
InChI=1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2
Microorganism:

No

IUPAC name(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
SMILESC1=CC(=C(C=C1C=CC(=O)O)O)O
InchiInChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
FormulaC9H8O4
PubChem ID689043
Molweight180.16
LogP1.2
Atoms13
Bonds2
H-bond Acceptor4
H-bond Donor3
Chemical Classificationbenzenoids acids carboxylic acids organic acids phenols
CHEBI-ID17395
Supernatural-IDSN0299986-01

mVOC Specific Details

Volatilization
The Henry's Law constant for caffeic acid is estimated as 1.4X10-16 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that caffeic acid is expected to be essentially nonvolatile from water surfaces(2). Caffeic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-7 mm Hg(SRC), determined from a fragment constant method(3).
Literature: (1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991) (2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990) (3) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
Soil Adsorption
The Koc of caffeic acid is estimated as 100(SRC), using a log Kow of 1.15(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that caffeic acid is expected to have high mobility in soil. The pKa of caffeic acid is 4.62(4), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb to organic carbon and clay more strongly than their neutral counterparts(5).
Literature: (1) Sangster J; LOGKOW Databank. Sangster Res. Lab., Montreal Quebec, Canada (1994) (2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990) (3) Swann RL et al; Res Rev 85: 17-28 (1983) (4) Serjeant EP, Dempsey B; Ionisation constants of organic acids in aqueous solution. IUPAC Chem Data Ser No. 23. NY, NY: Pergamon pp. 989 (1979) (5) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
MS-Links
Massbank-Links
Massbank Spectrum MSBNK-BGC_Munich-RP016701
Massbank Spectrum MSBNK-BGC_Munich-RP016702
Massbank Spectrum MSBNK-BGC_Munich-RP016703
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Massbank Spectrum MSBNK-Washington_State_Univ-BML80856
Massbank Spectrum MSBNK-Washington_State_Univ-BML80858

Species emitting the compound
KingdomSpeciesBiological FunctionOrigin/HabitatReference
EukaryotaFlammulina VelutipesnaKoreaKim et al. 2008
EukaryotaSparassis CrispanaKoreaKim et al. 2008
EukaryotaPhellinus LinteusnaKoreaKim et al. 2008
EukaryotaCoriolus Versicolorscavenging abilityFruska Gora low mountain chain, northern SerbiaKaraman et al. 2010
EukaryotaGanoderma Applanatumscavenging abilityFruska Gora low mountain chain, northern SerbiaKaraman et al. 2010
Method
KingdomSpeciesGrowth MediumApplied MethodVerification
EukaryotaFlammulina VelutipesnaHPLCyes
EukaryotaSparassis CrispanaHPLCyes
EukaryotaPhellinus LinteusnaHPLCyes
EukaryotaCoriolus VersicolornaHPLCyes
EukaryotaGanoderma ApplanatumnaHPLCyes