Milk Composition Database: Showing metabocard for Caffeic acid (BMDB0001964)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:49:13 UTC

Update Date

2020-05-11 20:48:55 UTC

MCDB ID

BMDB0001964

Secondary Accession Numbers

BMDB01964

Metabolite Identification

Common Name

Caffeic acid

Description

Caffeic acid, also known as caffeate, 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. Caffeic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Caffeic acid exists in all living species, ranging from bacteria to humans. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Dihydroxy-trans-cinnamate	ChEBI
3,4-Dihydroxycinnamic acid	ChEBI
trans-Caffeate	ChEBI
3,4-Dihydroxy-trans-cinnamic acid	Generator
3,4-Dihydroxycinnamate	Generator
Caffeate	Generator
Caffeic acid, monosodium salt	HMDB
Caffeic acid, (e)-isomer	HMDB
Sodium caffeate	HMDB
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3,4-Dihydroxycinnamic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)acrylic acid	HMDB
(e)-Caffeic acid	HMDB
3,4-Dihydroxybenzeneacrylic acid	HMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
3-(3,4-Dihydroxyphenyl)propenoic acid	HMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene	HMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzene	HMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzene	HMDB
DHCA	HMDB
trans-3,4-Dihydroxycinnamic acid	HMDB
Caffeic acid	HMDB
3',4'-Dihydroxycinnamic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid;	HMDB

Chemical Formula

C₉H₈O₄

Average Molecular Weight

180.1574

Monoisotopic Molecular Weight

180.042258744

IUPAC Name

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

Traditional Name

caffeic acid

CAS Registry Number

331-39-5

SMILES

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

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

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
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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	225 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.15	SANGSTER (1993)

Predicted Properties

Property	Value	Source
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-014i-1593000000-b24e97b50ed1f50252f3	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9800000000-bae43e98e22babcbf5a7	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9600000000-6140146b8e32bda5e3c9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0593000000-16610dfa8ac4ac67a4c2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-1593000000-b24e97b50ed1f50252f3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0592000000-1bb03bc99be6718d247e	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1900000000-6a963e50b910f05b6825	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00e9-5039000000-d55c6a31e04536d33b58	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-90ad608487db4c112469	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-dcc07d9a43defb5683a0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-762c7a39be8e2819bc51	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0019-4900000000-e716811ee5cf56acce9e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-037f59c6ff1daadca2a0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0019-6900000000-a67fe3c28be25c2fa72b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0019-1900000000-62d755ec157c381054b3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-6c93facd0d3caabc67f1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001r-0900000000-7b2d4553b6a25b853d4b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-3ed879b5217c5d703cd5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-bddc5a2872c93f7185ba	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9600000000-376ae5146fc0f93c9ff5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-7d707e3512f8df7d6c53	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-0900000000-c904417e68f103c0c963	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-03di-0900000000-f31bbdf32d6b72a381e7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-ad7b879926d9c809f9c8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014s-1900000000-d3c79213f8f23833fadc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-3adb4dbfdaeb614b61e6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-8f7413c3605b29515931	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2900000000-467621cde3e4486ad6bf	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-7fdae010c3ffe7ab1156	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000i-9000000000-a67e2178525a89f45da9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-8407d64b83bf427de33f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03dr-0900000000-91200c128446226f6ecb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-2ec4b8c30dbd96e11228	2021-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28306241	details

External Links

HMDB ID

HMDB0001964

DrugBank ID

DB01880

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Caffeic_acid

METLIN ID

Not Available

PubChem Compound

689043

PDB ID

Not Available

ChEBI ID

16433

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]

Showing metabocard for Caffeic acid (BMDB0001964)

Structure for BMDB0001964 (Caffeic acid)