Caffeic acid

C₉H₈O₄CAS 501-16-6180.16 g/mol

Open in Covalent MOL file

Alkene Carboxylic acid Phenol

Properties

Molecular formula: C₉H₈O₄
Molar mass: 180.16 g/mol
Exact mass: 180.0423 Da
Melting point: 196–198 °C
pKa: 4.62 (25 °C)
Water solubility: < 1 g/L (22.2 °C)
logP: 1.20Crippen estimate
Polar surface area: 77.8 Å²
H-bond donors / acceptors: 3 / 3
Rotatable bonds: 2
Double bonds: EE/Z, in SMILES order

Hazards

Warning

H315 Causes skin irritation62.7% of notifiers
H319 Causes serious eye irritation62.7% of notifiers
H335 May cause respiratory irritation61.4% of notifiers
H351 Suspected of causing cancer97.6% of notifiers
H361 Suspected of damaging fertility or the unborn child53% of notifiers

Aggregated from 83 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

Identifiers

CAS number

501-16-6

SMILES

O=C(O)/C=C/c1ccc(O)c(O)c1

InChIKey

QAIPRVGONGVQAS-DUXPYHPUSA-N

InChI

InChI=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+

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

14 names · show all

2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (2E)-
Cinnamic acid, 3,4-dihydroxy-, (E)-
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (E)-
Cinnamic acid, 3,4-dihydroxy-, trans-
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid
trans-Caffeic acid
trans-3,4-Dihydroxycinnamic acid
3,4-Dihydroxy-trans-cinnamic acid
(E)-Caffeic acid
(E)-3,4-Dihydroxycinnamic acid
(E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acid
(E)-3-(3,4-Dihydroxyphenyl)acrylic acid
ZINC 00058172

Work with Caffeic acid

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Caffeic acid331-39-5Stereo not defined

Similar compounds

Ferulic acid1135-24-666 % similar Isoferulic acid537-73-566 % similar Ferulic acid537-98-466 % similar p-Phenylenediacrylic acid16323-43-666 % similar P-Coumaric acid501-98-461 % similar p-Coumaric acid7400-08-061 % similar trans-3,4-Difluorocinnamic acid112897-97-958 % similar 3,4-Dichlorocinnamic acid1202-39-758 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue. All similar compounds

Same formula

5-Acetylsalicylic acid13110-96-8 p-Hydroxyphenylpyruvic acid156-39-8 Monomethyl terephthalate1679-64-7 Mono-methyl isophthalate1877-71-0 (4-Formylphenoxy)acetic acid22042-71-3 p-Acetoxybenzoic acid2345-34-8 Methyl 3-formyl-4-hydroxybenzoate24589-99-9 Phenylmalonic acid2613-89-0

Elsewhere

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