ChemFOnt: Showing chemical card for Trans-Caffeoyl tartaric acid (CFc000332880)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:26 UTC

Chemfont ID

CFc000332880

Molecule Identification

Common Name

Trans-Caffeoyl tartaric acid

Definition

Caftaric acid is a non-flavanoid that impacts the color of white wine. Caftaric acid is formed when caffeic acid and tartaric acid undergo esterification.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Caftarate	Generator
(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioate	HMDB
Caftaric acid	MeSH
trans-Caffeoyl tartarate	Generator

Chemical Formula

C₁₃H₁₂O₉

Average Molecular Weight

312.229

Monoisotopic Molecular Weight

312.048131982

IUPAC Name

(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

Traditional Name

caftaric acid

CAS Registry Number

67879-58-7

SMILES

O[C@H]([C@@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1

InChI Key

SWGKAHCIOQPKFW-JTNORFRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid ester
Coumaric acid or derivatives
Tricarboxylic acid or derivatives
Styrene
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Sugar acid
Fatty acid ester
Phenol
Beta-hydroxy acid
Fatty acyl
Benzenoid
Hydroxy acid
Alpha-hydroxy acid
Monosaccharide
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB13680)
Extracellular (HMDB: HMDB13680)

Source

Endogenous

Endogenous (HMDB: HMDB13680)

Plant

Plant (HMDB: HMDB13680)

Exogenous

Food

Food (HMDB: HMDB13680)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB13680)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	1.68	ALOGPS
logP	0.6	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	69.74 m³·mol⁻¹	ChemAxon
Polarizability	28.01 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