AFCDB: trans-Caffeic acid (FDB002559)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:25 UTC

Update date

2019-11-26 02:57:37 UTC

Primary ID

FDB002559

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

trans-Caffeic acid

Description

3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms.

CAS Number

501-16-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.61 g/L	ALOGPS
logP	1.67	ALOGPS
logP	1.53	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	17.34 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

C9H8O4

IUPAC name

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

InChI Key

QAIPRVGONGVQAS-DUXPYHPUSA-N

Isomeric SMILES

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

Average Molecular Weight

180.1574

Monoisotopic Molecular Weight

180.042258744

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
Coumaric acid or derivatives
Hydroxycinnamic acid
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

caffeic acid (CHEBI:16433 )
Caffeate derivatives (C01197 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 60.00%; H 4.48%; O 35.52%	DFC
Melting Point	Mp 223-225° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	1.35
Experimental pKa	pKa2 9.07 (25°)	DFC
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
GC-MS	Caffeic acid, 3 TMS, GC-MS Spectrum	splash10-014i-1593000000-b24e97b50ed1f50252f3	Spectrum
GC-MS	Caffeic acid, non-derivatized, GC-MS Spectrum	splash10-001i-9800000000-bae43e98e22babcbf5a7	Spectrum
GC-MS	Caffeic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9600000000-6140146b8e32bda5e3c9	Spectrum
GC-MS	Caffeic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0593000000-16610dfa8ac4ac67a4c2	Spectrum
GC-MS	Caffeic acid, non-derivatized, GC-MS Spectrum	splash10-014i-1593000000-b24e97b50ed1f50252f3	Spectrum
GC-MS	Caffeic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0592000000-1bb03bc99be6718d247e	Spectrum
Predicted GC-MS	Caffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-1900000000-6a963e50b910f05b6825	Spectrum
Predicted GC-MS	Caffeic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00e9-5039000000-d55c6a31e04536d33b58	Spectrum
Predicted GC-MS	Caffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-90ad608487db4c112469	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-dcc07d9a43defb5683a0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-762c7a39be8e2819bc51	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0019-4900000000-e716811ee5cf56acce9e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-037f59c6ff1daadca2a0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0019-6900000000-a67fe3c28be25c2fa72b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0019-1900000000-62d755ec157c381054b3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-6c93facd0d3caabc67f1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001r-0900000000-7b2d4553b6a25b853d4b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-3ed879b5217c5d703cd5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-bddc5a2872c93f7185ba	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9600000000-376ae5146fc0f93c9ff5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-7d707e3512f8df7d6c53	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-0900000000-c904417e68f103c0c963	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-03di-0900000000-f31bbdf32d6b72a381e7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-ad7b879926d9c809f9c8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014s-1900000000-d3c79213f8f23833fadc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-3adb4dbfdaeb614b61e6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-8f7413c3605b29515931	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2900000000-467621cde3e4486ad6bf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-7fdae010c3ffe7ab1156	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000i-9000000000-a67e2178525a89f45da9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-8407d64b83bf427de33f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03dr-0900000000-91200c128446226f6ecb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-2ec4b8c30dbd96e11228	2021-09-20	View Spectrum