ContaminantDB: cis-Sinapic acid

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

Record Information

Version

1.0

Creation Date

2016-05-26 00:16:26 UTC

Update Date

2016-11-09 01:18:38 UTC

Accession Number

CHEM028181

Identification

Common Name

cis-Sinapic acid

Class

Small Molecule

Description

A 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid in which the double bond has cis-configuration. It has been isolated from the shoots of alfalfa.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Z)-4-Hydroxy-3,5-dimethoxycinnamic acid	ChEBI
cis-4-Hydroxy-3,5-dimethoxycinnamic acid	ChEBI
(Z)-4-Hydroxy-3,5-dimethoxycinnamate	Generator
cis-4-Hydroxy-3,5-dimethoxycinnamate	Generator
cis-Sinapate	Generator
trans-Sinapinic acid	MeSH, HMDB
3,5-Dimethoxy-4-hydroxycinnamic acid	MeSH, HMDB
(e)-Sinapic acid	MeSH, HMDB
Sinapic acid	MeSH, HMDB
Sinapinic acid	MeSH, HMDB
Synapitic acid	MeSH, HMDB
4-Hydroxy-3,5-dimethoxycinnamic acid	MeSH, HMDB
trans-Sinapic acid	MeSH, HMDB
(2Z)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	HMDB
(Z)-3,5-Dimethoxy-4-hydroxycinnamic acid	HMDB
(Z)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid	HMDB
(Z)-Sinapic acid	HMDB
3,5-Dimethoxy-4-hydroxy-cis-cinnamic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	HMDB
Z-Sinapinic acid	HMDB
cis-Sinapic acid	HMDB
cis-Sinapinic acid	HMDB

Chemical Formula

C₁₁H₁₂O₅

Average Molecular Mass

224.210 g/mol

Monoisotopic Mass

224.068 g/mol

CAS Registry Number

7361-90-2

IUPAC Name

(2Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid

Traditional Name

(2Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid

SMILES

COC1=CC(\C=C/C(O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3-

InChI Key

PCMORTLOPMLEFB-ARJAWSKDSA-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
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid (CHEBI:76350 )

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	0.63 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.11	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.97 m³·mol⁻¹	ChemAxon
Polarizability	21.81 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
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00kr-3659000000-141953a5d5d848f1aa51	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00kr-3659000000-141953a5d5d848f1aa51	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-2958000000-16d208a44d4442af41c5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05di-1960000000-e20c10aa0bcc765f8c28	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0umi-8196000000-afceb35e7a5f28ec225c	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	splash10-056r-0190000000-6e81a94093485194a43f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1960000000-18717b9e874f0901ea68	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06vj-2900000000-254ee08e710708eb6545	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0190000000-89ae701e731ef1f24fd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0890000000-74c0bdbe7769b328017a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1910000000-69bbc48ce24397a342a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0290000000-9de305bfb1242c5c3e10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0980000000-368fb5936979c9a6e99d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-3900000000-395e080ff0323f7c60bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-cfca81bd3cf2894d0d6b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-e363c6280db16d0c6ea7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-8930000000-4fe3d11040b797e9d211	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

HMDB0034069

FooDB ID

FDB012318

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

1266059

ChEBI ID

76350

PubChem Compound ID

1549091

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

cis-Sinapic acid (CHEM028181)

Structure for CHEM028181: cis-Sinapic acid