ContaminantDB: Caffeic acid 4-sulfate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-27 01:34:39 UTC

Update Date

2016-11-09 01:22:30 UTC

Accession Number

CHEM041578

Identification

Common Name

Caffeic acid 4-sulfate

Class

Small Molecule

Description

Caffeic acid 4-O-sulfate (CAS: 1213651-94-5) is a polyphenol metabolite detected in biological fluids (PMID: 20428313). Caffeic acid sulfate was found to be elevated in rat urine after whole rye consumption which makes this compound a potential urinary biomarker of whole grain intake (PMID: 26862900).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Caffeate 4-O-sulfate	Generator
Caffeate 4-O-sulphate	Generator
Caffeic acid 4-O-sulfuric acid	Generator
Caffeic acid 4-O-sulphuric acid	Generator
Caffeate 4-sulfate	HMDB
Caffeate 4-sulphate	HMDB
Caffeic acid 4-sulfuric acid	HMDB
Caffeic acid 4-sulphuric acid	HMDB
(2E)-3-[3-Hydroxy-4-(sulfooxy)phenyl]prop-2-enoate	HMDB
(2E)-3-[3-Hydroxy-4-(sulphooxy)phenyl]prop-2-enoate	HMDB
(2E)-3-[3-Hydroxy-4-(sulphooxy)phenyl]prop-2-enoic acid	HMDB
(2E)-3-[3-Hydroxy-4-(sulfooxy)phenyl]-2-propenoic acid	HMDB
(e)-Caffeic acid 4-O-sulfate	HMDB
(e)-Caffeic acid 4-O-sulphate	HMDB
(e)-Caffeic acid 4-sulfate	HMDB
(e)-Caffeic acid 4-sulphate	HMDB
(e)-Caffeic acid sulfate	HMDB
(e)-Caffeic acid sulphate	HMDB
3-[3-Hydroxy-4-(sulfooxy)phenyl]-2-propenoic acid	HMDB
Caffeic acid 4-O-sulphate	HMDB
Caffeic acid 4-sulfate	HMDB
Caffeic acid 4-sulphate	HMDB
Caffeic acid sulfate	HMDB
Caffeic acid sulphate	HMDB
Caffeic acid-4'-sulfate	HMDB
Caffeic acid-4'-sulphate	HMDB
Caffeic acid-4’-sulfate	HMDB
Caffeic acid-4’-sulphate	HMDB
trans-Caffeic acid 4-O-sulfate	HMDB
trans-Caffeic acid 4-O-sulphate	HMDB
trans-Caffeic acid 4-sulfate	HMDB
trans-Caffeic acid 4-sulphate	HMDB
trans-Caffeic acid sulfate	HMDB
trans-Caffeic acid sulphate	HMDB
Caffeic acid 4-O-sulfate	HMDB

Chemical Formula

C₉H₈O₇S

Average Molecular Mass

260.221 g/mol

Monoisotopic Mass

259.999 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2E)-3-[3-hydroxy-4-(sulfooxy)phenyl]prop-2-enoic acid

Traditional Name

(2E)-3-[3-hydroxy-4-(sulfooxy)phenyl]prop-2-enoic acid

SMILES

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

InChI Identifier

InChI=1S/C9H8O7S/c10-7-5-6(2-4-9(11)12)1-3-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+

InChI Key

SNVAIAITQIIEMQ-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
Phenylsulfate
Arylsulfate
Phenoxy compound
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	-0.36	ALOGPS
logP	1.7	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	-2.4	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.01 m³·mol⁻¹	ChemAxon
Polarizability	22.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xu-1690000000-2099aa56bc17d6f8dfbc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dr-5029000000-f3ae7ef7834ca7b22d7d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-6d7405df313b60db279d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03xu-1980000000-2ff5233a16c02db10ab4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0690-8910000000-6a92b09121121f341ba8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-895e0889ba62c427ad9e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-0950000000-c8670832bae0b366e1c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03e9-4900000000-539439543f38aa904357	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0980000000-3dc7f107fbc65c3318a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0920000000-89701f174df8154819af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0900000000-55d19e06bcffd3a50179	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-2459f93a8b832017b2ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kb-7290000000-2342a5604ec0a33d21d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-b206397b87a65fe63d41	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0041708

FooDB ID

FDB031320

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

30777608

ChEBI ID

176485

PubChem Compound ID

21668705

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.

2. Ounnas F, Prive F, Salen P, Gaci N, Tottey W, Calani L, Bresciani L, Lopez-Gutierrez N, Hazane-Puch F, Laporte F, Brugere JF, Del Rio D, Demeilliers C, de Lorgeril M: Whole Rye Consumption Improves Blood and Liver n-3 Fatty Acid Profile and Gut Microbiota Composition in Rats. PLoS One. 2016 Feb 10;11(2):e0148118. doi: 10.1371/journal.pone.0148118. eCollection 2016.

3. Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510

Caffeic acid 4-sulfate (CHEM041578)

Structure for CHEM041578: Caffeic acid 4-sulfate