Showing chemical card for (2R)-3-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acid (CFc000222925)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:44:08 UTC

Chemfont ID

CFc000222925

Molecule Identification

Common Name

(2R)-3-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acid

Definition

3-(3,4-Dihydroxyphenyl)lactic acid, also known as a-hydroxyhydrocaffeic acid or danshensu, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-(3,4-Dihydroxyphenyl)lactic acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and rosemaries (Rosmarinus officinalis). This could make 3-(3,4-dihydroxyphenyl)lactic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-(3,4-Dihydroxyphenyl)lactic acid.

Structure

MOL SDF PDB SMILES InChI

SMILES for CFc000222925 ((2R)-3-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acid)

OC(CC1=CC=C(O)C(O)=C1)C(O)=O

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INCHI for CFc000222925 ((2R)-3-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acid)

InChI=1S/C9H10O5/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14/h1-3,8,10-12H,4H2,(H,13,14)

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Structure for CFc000222925 ((2R)-3-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acid)

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3D Structure for CFc000222925 ((2R)-3-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acid)

Synonyms

Value	Source
3-(3,4-Dihydroxyphenyl)lactate	ChEBI
3,4-Dihydroxyphenyllactic acid	Kegg
3,4-Dihydroxyphenyllactate	Generator
2-Hydroxy-3-(3,4-dihydroxyphenyl)propanoate	HMDB
2-Hydroxy-3-(3,4-dihydroxyphenyl)propanoic acid	HMDB
a-Hydroxyhydrocaffeic acid	HMDB
alpha-Hydroxyhydrocaffeate	HMDB
alpha-Hydroxyhydrocaffeic acid	HMDB
Danshensu	HMDB
DL-b-(3,4-Dihydroxyphenyl)lactic acid	HMDB
DL-beta-(3,4-Dihydroxyphenyl)lactic acid	HMDB
(3,4-Dihydroxyphenyl)lactic acid	HMDB
3,4-Dihydroxyphenyllactic acid, monosodium salt, (R)-isomer	HMDB
3,4-Dihydroxyphenyllactic acid, (+-)-isomer	HMDB
3,4-Dihydroxyphenyllactic acid, (R)-isomer	HMDB
3,4-Dihydroxyphenyllactic acid, monosodium salt, (+-)-isomer	HMDB
Salvianic acid a sodium	HMDB
3,4-Dihydroxyphenyllactic acid, monosodium salt	HMDB
2-Hydroxy-3-(3',4'-dihydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₅

Average Molecular Weight

198.1727

Monoisotopic Molecular Weight

198.05282343

IUPAC Name

3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid

Traditional Name

danshensu

CAS Registry Number

23028-17-3

SMILES

OC(CC1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C9H10O5/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14/h1-3,8,10-12H,4H2,(H,13,14)

InChI Key

PAFLSMZLRSPALU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Catechols
1-hydroxy-4-unsubstituted benzenoids
1-hydroxy-2-unsubstituted benzenoids
Benzene and substituted derivatives
Alpha hydroxy acids and derivatives
Secondary alcohols
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds

Substituents

3-phenylpropanoic-acid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:17807 )
2-hydroxy monocarboxylic acid (CHEBI:17807 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.7 g/L	ALOGPS
logP	0.77	ALOGPS
logP	0.58	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.42 m³·mol⁻¹	ChemAxon
Polarizability	18.4 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