Livestock Metabolome Database: Showing metabocard for trans-Ferulic acid (LMDB00287)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:30 UTC

Update Date

2016-07-19 23:24:27 UTC

Lmdb

LMDB00287

Secondary Accession Numbers

None

Metabolite Identification

Common Name

trans-Ferulic acid

Description

trans-Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. trans-Ferulic acid is a phenolic acid that can be absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/Kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernel. It occurs primarily in seeds and leaves both in its free form (rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet and xyloglucans in bamboo. It also can cross-link with proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), it readily forms a resonance stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reduce oxidative damage and amyloid pathology in Alzheimer disease. (PMID: 17127365 , 1398220 , 15453708 , 9878519 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	ChEBI
(e)-4'-Hydroxy-3'-methoxycinnamic acid	ChEBI
(e)-4-Hydroxy-3-methoxycinnamic acid	ChEBI
(e)-Ferulic acid	ChEBI
3-(4-Hydroxy-3-methoxyphenyl)propenoic acid	ChEBI
3-Methoxy-4-hydroxy-trans-cinnamic acid	ChEBI
4-Hydroxy-3-methoxycinnamic acid	ChEBI
trans-4-Hydroxy-3-methoxycinnamic acid	ChEBI
3-Methoxy-4-hydroxy-trans-cinnamate	Kegg
4-Hydroxy-3-methoxycinnamate	Kegg
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate	Generator
(e)-4'-Hydroxy-3'-methoxycinnamate	Generator
(e)-4-Hydroxy-3-methoxycinnamate	Generator
(e)-Ferulate	Generator
3-(4-Hydroxy-3-methoxyphenyl)propenoate	Generator
trans-4-Hydroxy-3-methoxycinnamate	Generator
trans-Ferulate	Generator
Ferulate	Generator
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate	HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	HMDB
(e)-4-Hydroxy-3-methoxy-cinnamate	HMDB
(e)-4-Hydroxy-3-methoxy-cinnamic acid	HMDB
Ferulic acid, (e)-isomer	MeSH, HMDB
Ferulic acid, monosodium salt	MeSH, HMDB
Sodium ferulate	MeSH, HMDB
Ferulic acid, (Z)-isomer	MeSH, HMDB
8,8'-Diferulic acid	MeSH, HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acid	HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid	HMDB
(E)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid	HMDB
Fumalic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	HMDB
3-Methoxy-4-hydroxycinnamic acid	HMDB
4'-Hydroxy-3'-methoxycinnamic acid	HMDB
Coniferic acid	HMDB
Ferulaic acid	HMDB
4’-Hydroxy-3’-methoxycinnamic acid	PhytoBank

Chemical Formula

C₁₀H₁₀O₄

Average Molecular Weight

194.184

Monoisotopic Molecular Weight

194.057908808

IUPAC Name

(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

Traditional Name

ferulic acid

CAS Registry Number

537-98-4

SMILES

COC1=C(O)C=CC(\C=C\C(O)=O)=C1

InChI Identifier

InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

InChI Key

KSEBMYQBYZTDHS-HWKANZROSA-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
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
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

ferulic acids (CHEBI:17620 )
Coniferyl alcohol derivatives (C01494 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.58	ALOGPS
logP	1.67	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.5 m³·mol⁻¹	ChemAxon
Polarizability	19.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-05g4-1978000000-1097d5b300514a0489df	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00kv-2964000000-3d20d62c97c33247cfcf	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00ku-1965000000-ebee2a916fe97f0270a1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9654000000-b3f1759076cffd2ac235	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-000m-3975000000-5a41c311d78f7219474c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-1900000000-5dffac87fe7c815de4ce	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2900000000-8db541bacfe47b9e0c8b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2900000000-a338415bd30d4e62e664	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05g4-1978000000-1097d5b300514a0489df	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kv-2964000000-3d20d62c97c33247cfcf	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ku-1965000000-ebee2a916fe97f0270a1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9654000000-b3f1759076cffd2ac235	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000m-3975000000-5a41c311d78f7219474c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kv-1954000000-9dae07505bd18466be87	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002e-0900000000-d76b7991f2d90cb58bd5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6094000000-b805979df23a0d890d7c	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 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 (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0900000000-d193da7a6efffdab2dbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kr-7900000000-b5b8d28b28c8067c3932	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002r-9000000000-d3616a5367a7a2a9b3c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0006-1900000000-5dffac87fe7c815de4ce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-c173873ef0d975be6c34	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-0b9174ecaba08b2f01b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-1900000000-eff77e27aef254928643	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001r-9700000000-18946fad05ffb1f78a7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001r-9300000000-e2221a73d3d078bf6e03	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-653c9a454414dd8b8b50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-002b-0900000000-62b2ee8bf9571be3d97f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-a7cded21e6010eb8bce2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-c173873ef0d975be6c34	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0900000000-0b9174ecaba08b2f01b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-1900000000-eff77e27aef254928643	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001r-9700000000-18946fad05ffb1f78a7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001r-9300000000-e2221a73d3d078bf6e03	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-a7cded21e6010eb8bce2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-002b-0900000000-cdced9ddbcdaedf2f1b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0900000000-434fdd914ca34cd68f41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-0dcbcad8bf6cb403f4f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g31-5900000000-4fa9ed831b4e0d1573e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-29c8691e15490f8d88ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-e940f09e099b7acf3772	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00o1-1900000000-ee61087a069406e459c7	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-5900000000-8c81de6c352294475072	Spectrum
1D NMR	1H 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
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Ruminal Fluid	Detected and Quantified	4.41 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	11.8 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	11.9 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	13.6 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	17.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	20.4 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	13 +/- 3 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	20.6 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	17 +/- 8 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	17 +/- 8 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	20 +/- 4 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	20 +/- 11 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	8 +/- 5 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	3.91 uM	Not Available	Bovine	Burim NA, Qendrim...	details

External Links

DrugBank ID

HMDB ID

FooDB ID

Phenol Explorer ID

KNApSAcK ID

BiGG ID

Not Available

BioCyc ID

FERULIC-ACID

METLIN ID

4156

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mancuso C, Scapagini G, Curro D, Giuffrida Stella AM, De Marco C, Butterfield DA, Calabrese V: Mitochondrial dysfunction, free radical generation and cellular stress response in neurodegenerative disorders. Front Biosci. 2007 Jan 1;12:1107-23. [17127365 ]
Graf E: Antioxidant potential of ferulic acid. Free Radic Biol Med. 1992 Oct;13(4):435-48. [1398220 ]
Fukuoka K, Sawabe A, Sugimoto T, Koga M, Okuda H, Kitayama T, Shirai M, Komai K, Komemushi S, Matsuda K: Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138. J Agric Food Chem. 2004 Oct 6;52(20):6326-9. [15453708 ]
Bourne LC, Rice-Evans C: Bioavailability of ferulic acid. Biochem Biophys Res Commun. 1998 Dec 18;253(2):222-7. [9878519 ]

Showing metabocard for trans-Ferulic acid (LMDB00287)

Structure for LMDB00287 (trans-Ferulic acid)