ContaminantDB: 4-8',5'-5''-Dehydrotriferulic acid

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

Record Information

Version

1.0

Creation Date

2016-05-25 20:46:35 UTC

Update Date

2016-11-09 01:17:37 UTC

Accession Number

CHEM023000

Identification

Common Name

4-8',5'-5''-Dehydrotriferulic acid

Class

Small Molecule

Description

4-O-8',5'-5''-Dehydrotriferulic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313)

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-O-8',5'-5''-Dehydrotriferulate	Generator
5-5',8'-O-4''-Triferulic acid	HMDB
(2Z)-3-{5'-[(1E)-2-carboxyeth-1-en-1-yl]-2',6-dihydroxy-3',5-dimethoxy-[1,1'-biphenyl]-3-yl}-2-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}prop-2-enoate	HMDB
4-8',5'-5''-Dehydrotriferulate	HMDB

Chemical Formula

C₃₀H₂₆O₁₂

Average Molecular Mass

578.520 g/mol

Monoisotopic Mass

578.142 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2Z)-3-(3-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-4-hydroxy-5-methoxyphenyl)-2-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}prop-2-enoic acid

Traditional Name

(2Z)-3-(3-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-4-hydroxy-5-methoxyphenyl)-2-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}prop-2-enoic acid

SMILES

COC1=CC(\C=C\C(O)=O)=CC=C1O\C(=C/C1=CC(OC)=C(O)C(=C1)C1=CC(\C=C\C(O)=O)=CC(OC)=C1O)C(O)=O

InChI Identifier

InChI=1S/C30H26O12/c1-39-22-12-16(5-8-26(31)32)4-7-21(22)42-25(30(37)38)15-18-11-20(29(36)24(14-18)41-3)19-10-17(6-9-27(33)34)13-23(40-2)28(19)35/h4-15,35-36H,1-3H3,(H,31,32)(H,33,34)(H,37,38)/b8-5+,9-6+,25-15-

InChI Key

PIXLMMCJKULCET-VVYRROKUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
Enol-phenylpyruvate
Phenoxyacetate
Methoxyphenol
Tricarboxylic acid or derivatives
Anisole
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Phenol
Ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	0.0029 g/L	ALOGPS
logP	3.93	ALOGPS
logP	4.31	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	2.77	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	151.78 m³·mol⁻¹	ChemAxon
Polarizability	58.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01si-0302090000-8ef4564680c6a634f372	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0kif-6033019000-fa2df057f297b10b8f10	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("4-O-8',5'-5''-Dehydrotriferulic acid,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_8) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0001090000-91b81007e5937f5817eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00o3-0404190000-e50937b30530078f87f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052o-0908000000-bcdc9e3867bebd3107db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kr-0000690000-c3709fba9d1d7936eb53	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-0000690000-0c09d0e12a8ce59c52f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05n0-0206790000-614b6c9e900319bd55fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01tc-0002090000-f0de6520b7cec4db0a89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02ar-0102190000-67ba224b8eddce9a1e98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-005i-0947530000-1ce5de0c005ada140047	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000090000-e95ba0234b0d93616324	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02tc-0200090000-46f9e68aa9d5c159234b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0902010000-eef0735ca6768fe2cc3d	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

HMDB0029298

FooDB ID

FDB000306

Phenol Explorer ID

562

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

28637678

ChEBI ID

176125

PubChem Compound ID

71578617

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Rouau X, Cheynier V, Surget A, Gloux D, Barron C, Meudec E, Louis-Montero J, Criton M: A dehydrotrimer of ferulic acid from maize bran. Phytochemistry. 2003 Aug;63(8):899-903.

2. Bunzel M, Ralph J, Bruning P, Steinhart H: Structural identification of dehydrotriferulic and dehydrotetraferulic acids isolated from insoluble maize bran fiber. J Agric Food Chem. 2006 Aug 23;54(17):6409-18.

3. 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.

4-8',5'-5''-Dehydrotriferulic acid (CHEM023000)

Structure for CHEM023000: 4-8',5'-5''-Dehydrotriferulic acid