Showing Compound Pinosylvin (FDB002541)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:25 UTC

Update date

2019-11-26 02:57:35 UTC

Primary ID

FDB002541

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pinosylvin

Description

Pinosylvin, also known as 5-[(Z)-2-phenylvinyl]benzene-1,3-diol, is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Pinosylvin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pinosylvin can be found in beer and grape wine, which makes pinosylvin a potential biomarker for the consumption of these food products. Pinosylvin is a pre-infectious stilbenoid toxin (i.e. synthesized prior to infection), contrary to phytoalexins which are synthesized during infection. It is present in the heartwood of Pinaceae. It is a fungitoxin protecting the wood from fungal infection. It is also found in Gnetum cleistostachyum .

CAS Number

102-61-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(E)-3,5-stilbenediol	biospider
(E)-5-(2-Phenylethenyl)-1,3-benzenediol	biospider
(trans)-3,5-stilbenediol	biospider
1,3-Benzenediol, 5-(2-phenylethenyl)-	biospider
1,3-Benzenediol, 5-(2-phenylethenyl)-, (E)-	biospider
1,3-Benzenediol, 5-(2-phenylethenyl)-, (E)- (9CI)	biospider
1-(3,5-Dihydroxyphenyl)-2-phenylethylene	db_source
3,5-Stilbenediol	db_source
3,5-Stilbenediol, (E)-	biospider
5-(2-phenylethenyl)-1,3-benzenediol	biospider

Showing 1 to 10 of 20 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	3.28	ALOGPS
logP	3.71	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.47 m³·mol⁻¹	ChemAxon
Polarizability	22.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C14H12O2

IUPAC name

5-[(Z)-2-phenylethenyl]benzene-1,3-diol

InChI Identifier

InChI=1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6-

InChI Key

YCVPRTHEGLPYPB-SREVYHEPSA-N

Isomeric SMILES

OC1=CC(\C=C/C2=CC=CC=C2)=CC(O)=C1

Average Molecular Weight

212.2439

Monoisotopic Molecular Weight

212.083729628

Classification

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

pinosylvin (CHEBI:36010 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 79.23%; H 5.70%; O 15.08%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0190000000-270584687f920cebf413	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0690000000-e1a47958387c6d34e58d	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-3900000000-fbafa88fc9263215b47a	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-0e7729e71983b52810e5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0190000000-3d6c47aeb5389bd3b9f9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02bf-3920000000-f27583e839ba2fcd4065	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C01745

Pubchem Compound ID

5280457

Pubchem Substance ID

Not Available

ChEBI ID

36011

Phenol-Explorer ID

590

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CMH59-G:CMH59-G

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00002897

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Grape	Expected but not quantified	Not Available	PHYTOHUB
Peanut	Expected but not quantified	Not Available	PHYTOHUB

Showing 1 to 2 of 2 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Showing Compound Pinosylvin (FDB002541)

Structure for FDB002541 (Pinosylvin)