ChemFOnt: Showing chemical card for cis-Caffeic acid (CFc000001904)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:39 UTC

Chemfont ID

CFc000001904

Molecule Identification

Common Name

cis-Caffeic acid

Definition

Caffeic acid, also known as caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid exists in all living species, ranging from bacteria to humans. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. Outside of the human body, caffeic acid has been detected, but not quantified in fats and oils and nuts. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Caffeic acid has a variety of potential pharmacological effects in in vitro studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human HT-1080 fibrosarcoma cell line has recently been established. It occurs at high levels in black chokeberry (141 mg per 100 g) and in fairly high level in lingonberry (6 mg per 100 g).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Dihydroxy-trans-cinnamate	ChEBI
3,4-Dihydroxycinnamic acid	ChEBI
trans-Caffeate	ChEBI
3,4-Dihydroxy-trans-cinnamic acid	Generator
3,4-Dihydroxycinnamate	Generator
Caffeate	Generator
Caffeic acid, monosodium salt	HMDB
Caffeic acid, (e)-isomer	HMDB
Sodium caffeate	HMDB
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3,4-Dihydroxycinnamic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)acrylic acid	HMDB
(e)-Caffeic acid	HMDB
3,4-Dihydroxybenzeneacrylic acid	HMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
3-(3,4-Dihydroxyphenyl)propenoic acid	HMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene	HMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzene	HMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzene	HMDB
DHCA	HMDB
trans-3,4-Dihydroxycinnamic acid	HMDB
Caffeic acid	HMDB
3',4'-Dihydroxycinnamic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid;	HMDB

Chemical Formula

C₉H₈O₄

Average Molecular Weight

180.1574

Monoisotopic Molecular Weight

180.042258744

IUPAC Name

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

Traditional Name

caffeic acid

CAS Registry Number

4361-87-9

SMILES

OC(=O)\C=C\C1=CC(O)=C(O)C=C1

InChI Identifier

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+

InChI Key

QAIPRVGONGVQAS-DUXPYHPUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

caffeic acid (CHEBI:16433 )
Caffeate derivatives (C01197 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0003501)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Nut

Nuts (FooDB: FOOD00869)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.61 g/L	ALOGPS
logP	1.67	ALOGPS
logP	1.53	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	17.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon