Showing Compound 2-Furancarboxylic acid (FDB000951)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:46 UTC

Update date

2020-04-21 18:02:08 UTC

Primary ID

FDB000951

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Furancarboxylic acid

Description

Isolated from roots of Phaseolus vulgaris (kidney bean) Furoic acid is a metabolite that appears in the urine of workers occupationally exposed to furfural and is marker of exposure to this compound. Furfural is a heterocyclic aldehyde that is commonly used as a solvent in industry. It is readily absorbed into the body via the lungs and has significant skin absorption. Furfural is an irritant of the eyes, mucous membranes, and skin and is a central nervous system depressant. Furfural as a confirmed animal carcinogen with unknown relevance to humans (It has been suggested that is a substance that produces hepatic cirrhosis). Once in the body, furfural is metabolized rapidly via oxidation to the metabolite furoic acid, which is then conjugated with glycine and excreted in the urine in both free and conjugated forms. (PMID: 3751566, 4630229, 12587683). Furoic acid is a biomarker for the consumption of beer.

CAS Number

88-14-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Carboxyfuran	ChEBI
2-Furancarboxylic acid	ChEBI
2-Furanoic acid	ChEBI
Acide 2-furoique	ChEBI
Acido 2-furoico	ChEBI
alpha-Furancarboxylic acid	ChEBI
alpha-Furoic acid	ChEBI
Furan-2-carbonsaeure	ChEBI
Pyromucic acid	ChEBI
2-Furancarboxylate	Generator
2-Furanoate	Generator
a-Furancarboxylate	Generator
a-Furancarboxylic acid	Generator
alpha-Furancarboxylate	Generator
Α-furancarboxylate	Generator
Α-furancarboxylic acid	Generator
a-Furoate	Generator
a-Furoic acid	Generator
alpha-Furoate	Generator
Α-furoate	Generator
Α-furoic acid	Generator
Pyromucate	Generator
2-Furoate	Generator
b-Furancarboxylate	HMDB
b-Furancarboxylic acid	HMDB
b-Furoate	HMDB
b-Furoic acid	HMDB
beta-Furancarboxylate	HMDB
beta-Furancarboxylic acid	HMDB
beta-Furoate	HMDB
beta-Furoic acid	HMDB
Furancarboxylate	HMDB
Furancarboxylic acid	HMDB
Furoate	HMDB
Furoic acid	HMDB
Furan-3-carboxylic	HMDB
2-Furoic acid, sodium salt	HMDB
Furan-2-ylacetate	HMDB
Furan-2-carboxylate	HMDB
2-Furoic acid	KEGG
Furan-2-carboxylic acid	PhytoBank
α-furancarboxylic acid	biospider
α-furoic acid	biospider
2-furancarboxilic acid	biospider
2-Furoic acid [per EINECS]	biospider
2-Furoic acid, 8CI	db_source
2-FUROIC ACID, PRACT	biospider
A-furancarboxylate	biospider
A-furancarboxylic acid	biospider
A-furoate	biospider
Alpha-furancarboxylate	biospider
Alpha-furancarboxylic acid	biospider
Alpha-furoate	biospider
Alpha-furoic acid	biospider
B-furancarboxylate	biospider
B-furancarboxylic acid	biospider
B-furoate	biospider
B-furoic acid	biospider
Beta-furancarboxylate	biospider
Beta-furancarboxylic acid	biospider
Beta-furoate	biospider
Beta-furoic acid	biospider
FOA	biospider
Furancarboxylic acid-(2)	biospider
Furoica	biospider
α-furancarboxylate	Generator
α-furancarboxylic acid	Generator
α-furoate	Generator
α-furoic acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	27.1 g/L	ALOGPS
logP	0.98	ALOGPS
logP	0.69	ChemAxon
logS	-0.62	ALOGPS
pKa (Strongest Acidic)	-6.5	ChemAxon
pKa (Strongest Basic)	6.41	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	25.71 m³·mol⁻¹	ChemAxon
Polarizability	9.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H4O3

IUPAC name

furan-2-carboxylic acid

InChI Identifier

InChI=1S/C5H4O3/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)

InChI Key

SMNDYUVBFMFKNZ-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C1=CC=CO1

Average Molecular Weight

112.0835

Monoisotopic Molecular Weight

112.016043994

Classification

Description

Belongs to the class of organic compounds known as furoic acids. These are organic compounds containing a furoic acid moiety, with a structure characterized by a furan ring bearing a carboxylic acid group at the C2 or C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furans

Sub Class

Furoic acid and derivatives

Direct Parent

Furoic acids

Alternative Parents

Substituents

Furoic acid
Heteroaromatic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

furoic acid (CHEBI:30845 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 53.58%; H 3.60%; O 42.82%	DFC
Melting Point	Mp 133-134°	DFC
Boiling Point	Bp20 141-144°	DFC
Experimental Water Solubility	37.1 mg/mL at 15 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	0.64	POMONA (1987)
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
GC-MS	2-Furancarboxylic acid, 1 TMS, GC-MS Spectrum	splash10-004i-2900000000-0a68833fc4193e1f8ced	Spectrum
GC-MS	2-Furancarboxylic acid, non-derivatized, GC-MS Spectrum	splash10-004i-2900000000-0a68833fc4193e1f8ced	Spectrum
GC-MS	2-Furancarboxylic acid, non-derivatized, GC-MS Spectrum	splash10-004j-4900000000-ea5ecbab959d0d5c46f2	Spectrum
Predicted GC-MS	2-Furancarboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01p6-9200000000-29936ed9a6e09458beeb	Spectrum
Predicted GC-MS	2-Furancarboxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00ds-9200000000-deea8b11e937a3c9a0b6	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-014i-9000000000-29104923ddd1637492b6	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-014i-9000000000-f5839ae3e2498c8ed422	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-014m-9000000000-add36932dee552c27460	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-3900000000-1400c95fd6fa180f3477	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-9000000000-3ef00380e59fd05e13d7	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-9000000000-793fd8d927620ba879c4	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00kb-9000000000-41d0eb8e5d92a9c18133	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-9000000000-b316782c64a0bd01cfa4	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-3900000000-1400c95fd6fa180f3477	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-9000000000-3ef00380e59fd05e13d7	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-9000000000-793fd8d927620ba879c4	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kb-9000000000-41d0eb8e5d92a9c18133	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-b316782c64a0bd01cfa4	Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-03di-0900000000-e56f9404be174f693636	Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-03di-4900000000-d5a109e334b699d07fd4	Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-0002-9200000000-5ffc1a1c60bdd1e1607f	Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 16V, positive	splash10-0002-9000000000-c8b314b1b859572c9810	Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 20V, positive	splash10-0002-9000000000-557bd61baaf69da1bbf3	Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-0002-9000000000-dc124ecf6a6750677b10	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-8900000000-0e807897f25b2ae739ec	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-9400000000-a38fb6802bc09c6a697f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uy1-9000000000-88ac4d1b946f0141be71	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-23013259dcdc1acd4316	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-9600000000-197797d0dbb1a04c891c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-9000000000-b09281ae3a89c2ed52ed	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16739

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00617

CRC / DFC (Dictionary of Food Compounds) ID

BNJ06-U:BNJ06-U

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00000151

HET ID

FOA

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1040161

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference