Showing Compound 5-Hydroxyferulic acid (FDB014170)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:07 UTC

Update date

2019-11-26 03:09:37 UTC

Primary ID

FDB014170

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5-Hydroxyferulic acid

Description

5-Hydroxyferulic acid, also known as trans-5-hydroxyferulate, 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. 5-Hydroxyferulic acid has been detected, but not quantified in, several different foods, such as common chokecherries (Prunus virginiana), cupuaçus (Theobroma grandiflorum), persimmons (Diospyros), black huckleberries (Gaylussacia baccata), and climbing beans (Vigna umbellata). This could make 5-hydroxyferulic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Hydroxyferulic acid.

CAS Number

1782-55-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoic acid	ChEBI
3-Methoxy-4,5-dihydroxy-trans-cinnamic acid	ChEBI
trans-5-Hydroxyferulic acid	ChEBI
(2E)-3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoate	Generator
3-Methoxy-4,5-dihydroxy-trans-cinnamate	Generator
trans-5-Hydroxyferulate	Generator
5-Hydroxyferulate	Generator
3,4-Dihydroxy-5-methoxycinnamoic acid	HMDB
3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid, 9ci	HMDB
3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoic acid	HMDB
3-Methoxycaffeic acid	HMDB
5-Hydroxyferulic acid	HMDB
HFL	HMDB
5-Hydroxyferulate methyl ester	Generator
3-(3,4-Dihydroxy-5-methoxy)-2-propenoate	Generator
3,4-Dihydroxy-5-methoxycinnamic acid	HMDB
E-5-Hydroxyferulic acid	HMDB
3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid	HMDB
2-Propenoic acid, 3-(3,4-dihydroxy-5-methoxyphenyl)-	biospider
3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid, 9CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	1.04 g/L	ALOGPS
logP	1.41	ALOGPS
logP	1.37	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.48 m³·mol⁻¹	ChemAxon
Polarizability	20.31 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

Chemical Formula

C10H10O5

IUPAC name

(2E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid

InChI Identifier

InChI=1S/C10H10O5/c1-15-8-5-6(2-3-9(12)13)4-7(11)10(8)14/h2-5,11,14H,1H3,(H,12,13)/b3-2+

InChI Key

YFXWTVLDSKSYLW-NSCUHMNNSA-N

Isomeric SMILES

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

Average Molecular Weight

210.1834

Monoisotopic Molecular Weight

210.05282343

Classification

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
Hydroxycinnamic acid
Coumaric acid or derivatives
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
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

hydroxycinnamic acid (CHEBI:2069 )
Coniferyl alcohol derivatives (C05619 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Animal

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 57.14%; H 4.80%; O 38.06%	DFC
Melting Point	Mp 182° (168-170° dec)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	5-Hydroxyferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dl-0910000000-edb7cb180844171b184b	Spectrum
Predicted GC-MS	5-Hydroxyferulic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-6039700000-818fd1c6815f0b1bf5f0	Spectrum
Predicted GC-MS	5-Hydroxyferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0970000000-6f1608973608646a6815	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02tc-1910000000-99bedde5d4b95d2a72ea	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4s-3900000000-db5c30fefbe69f4bf23a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0290000000-25c9e8b31be5cda28840	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0950000000-6b6628733be09dd12dec	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000g-2900000000-426d3db7318485c7e916	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0aor-0690000000-3d076d9d2c8322ea32d8	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ls-0900000000-075ce6e6c6eb242ff7c2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052b-3920000000-b91d58bedeef6007bb24	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0910000000-198b07c641d6eb666e07	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0296-0910000000-229335782ae991df2203	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-9600000000-365cec17f27513fd8043	2021-09-24	View Spectrum