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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:52:39 UTC

Update Date

2023-02-21 17:22:45 UTC

HMDB ID

HMDB0032914

Secondary Accession Numbers

HMDB32914

Metabolite Identification

Common Name

2-Furancarboxaldehyde

Description

2-Furancarboxaldehyde, also known as 2-furaldehyde or a-furole, belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. 2-Furancarboxaldehyde is found in allspice and it is also a flavour ingredient. 2-Furancarboxaldehyde is present in coffee, calamus, matsutake mushroom (Tricholoma matsutake), pumpkin, malt, peated malt, Bourbon vanilla, Lamb's lettuce, pimento leaf and various fruits, e.g. apple, apricot, sweet cherry, morello cherry, orange, grapefruit, Chinese quince and a common constituent of essential oils. Furfural is an organic compound derived from a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Formylfuran	ChEBI
2-Furaldehyde	ChEBI
2-Furanaldehyde	ChEBI
2-Furancarbonal	ChEBI
2-Furyl-methanal	ChEBI
2-Furylcarboxaldehyde	ChEBI
Furaldehyde	ChEBI
2-Formyl furan	HMDB
2-Formylofuran	HMDB
2-Furaldehyde, 8ci	HMDB
2-Furancarboxyaldehyde	HMDB
2-Furfural	HMDB
2-Furfuraldehyde	HMDB
2-Furylaldehyde	HMDB
2-Furylaldehyde xypropane	HMDB
2-Furylmethanal	HMDB
a-Furfuraldehyde	HMDB
a-Furole	HMDB
alpha-Furfuraldehyde	HMDB
alpha-Furole	HMDB
FEMA 2489	HMDB
Fural	HMDB
Furale	HMDB
Furan-2-aldehyde	HMDB
Furan-2-carbaldehyde	HMDB
Furan-2-carboxaldehyde	HMDB
Furancarbonal	HMDB
Furfural	HMDB
Furfuraldehyde	HMDB
Furfurale	HMDB
Furfuralu	HMDB
Furfurol	HMDB
Furfurole	HMDB
Furfurylaldehyde	HMDB
Furol	HMDB
Furole	HMDB
Furyl-methanal	HMDB
2-Furancarboxaldehyde	ChEBI

Chemical Formula

C₅H₄O₂

Average Molecular Weight

96.0841

Monoisotopic Molecular Weight

96.021129372

IUPAC Name

furan-2-carbaldehyde

Traditional Name

bran oil

CAS Registry Number

98-01-1

SMILES

O=CC1=CC=CO1

InChI Identifier

InChI=1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H

InChI Key

HYBBIBNJHNGZAN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-aldehydes

Alternative Parents

Substituents

Aryl-aldehyde
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

furans (CHEBI:34768 )
aldehyde (CHEBI:34768 )
a small molecule (CPD0-2357 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032914)
Cytoplasm (HMDB: HMDB0032914)

Excreta

Biofluid or Excreta

Urine (PMID: 22284503)
Feces (PMID: 17314143)

Beer (FooDB: FOOD00268)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)
Rice (FooDB: FOOD00125)

Flat bread

Tortilla (FooDB: FOOD00709)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Cabbage

Cauliflower (FooDB: FOOD00031)

Root vegetable

Celeriac (FooDB: FOOD00214)
Kohlrabi (FooDB: FOOD00033)

Mushroom

Tuber

Potato (FooDB: FOOD00175)

Leaf vegetable

Common beet (FooDB: FOOD00025)
Rocket salad (ssp.) (FooDB: FOOD00077)

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Herb and spice

Herb

Spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Tropical fruit

Guava (FooDB: FOOD00150)
Mango (FooDB: FOOD00106)
Tamarind (FooDB: FOOD00180)

Citrus

Lime (FooDB: FOOD00053)
Citrus (FooDB: FOOD00859)

Drupe

Sweet cherry (FooDB: FOOD00145)

Berry

Pome

Pomes (FooDB: FOOD00856)

Fruits (FooDB: FOOD00871)

Snack

Tortilla chip (FooDB: FOOD00721)

Dish

Tex-mex cuisine

Taco (FooDB: FOOD00708)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0032914)
Insecticide (HMDB: HMDB0032914)

Pesticide (HMDB: HMDB0032914)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0032914)

Pharmaceutical industry

Biomarker

Celiac disease (MarkerDB: MDB00029831)

Biological role

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-37 °C	Not Available
Boiling Point	161.00 to 162.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	74.1 mg/mL at 25 °C	Not Available
LogP	0.41	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	15.4 g/L	ALOGPS
logP	0.43	ALOGPS
logP	0.75	ChemAxon
logS	-0.79	ALOGPS
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	25.03 m³·mol⁻¹	ChemAxon
Polarizability	8.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	115.475	31661259
DarkChem	[M-H]-	111.951	31661259
DeepCCS	[M+H]+	124.425	30932474
DeepCCS	[M-H]-	122.473	30932474
DeepCCS	[M-2H]-	157.909	30932474
DeepCCS	[M+Na]+	132.162	30932474
AllCCS	[M+H]+	119.2	32859911
AllCCS	[M+H-H2O]+	114.1	32859911
AllCCS	[M+NH4]+	124.0	32859911
AllCCS	[M+Na]+	125.4	32859911
AllCCS	[M-H]-	115.4	32859911
AllCCS	[M+Na-2H]-	118.4	32859911
AllCCS	[M+HCOO]-	121.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Furancarboxaldehyde	O=CC1=CC=CO1	1403.6	Standard polar	33892256
2-Furancarboxaldehyde	O=CC1=CC=CO1	803.7	Standard non polar	33892256
2-Furancarboxaldehyde	O=CC1=CC=CO1	851.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Furancarboxaldehyde EI-B (Non-derivatized)	splash10-0002-9000000000-316042e81451a85c85c7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Furancarboxaldehyde CI-B (Non-derivatized)	splash10-0002-9000000000-c11251a363a8758eff6f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Furancarboxaldehyde EI-B (Non-derivatized)	splash10-0002-9000000000-34f068d9c1909d5f383c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Furancarboxaldehyde EI-B (Non-derivatized)	splash10-000b-9000000000-0ba2bcde82e913fd4d05	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Furancarboxaldehyde EI-B (Non-derivatized)	splash10-0002-9000000000-316042e81451a85c85c7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Furancarboxaldehyde CI-B (Non-derivatized)	splash10-0002-9000000000-c11251a363a8758eff6f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Furancarboxaldehyde EI-B (Non-derivatized)	splash10-0002-9000000000-34f068d9c1909d5f383c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Furancarboxaldehyde EI-B (Non-derivatized)	splash10-000b-9000000000-0ba2bcde82e913fd4d05	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Furancarboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-6a50101e12b2852abfe7	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Furancarboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000b-9000000000-cd9428558cbd2156d088	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Furancarboxaldehyde QqQ 6V, positive-QTOF	splash10-0002-9000000000-34878f09e7d18412233f	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Furancarboxaldehyde QqQ 8V, positive-QTOF	splash10-0002-9000000000-bb81928ea0c2d7f88664	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Furancarboxaldehyde QqQ 10V, positive-QTOF	splash10-0002-9000000000-90b37a6cd63355b3a713	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Furancarboxaldehyde QqQ 12V, positive-QTOF	splash10-00kb-9000000000-317bc9f8152533afdd52	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Furancarboxaldehyde QqQ 14V, positive-QTOF	splash10-00kb-9000000000-a11f00c420760e9640e0	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Furancarboxaldehyde QqQ 16V, positive-QTOF	splash10-014m-9000000000-52b42b52d2b2e640a495	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Furancarboxaldehyde QqQ 18V, positive-QTOF	splash10-014m-9000000000-b52b7726258822afc225	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 10V, Positive-QTOF	splash10-0002-9000000000-51503229d4632a8e7416	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 20V, Positive-QTOF	splash10-0002-9000000000-6ae7dc2ce8bff7c66af8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 40V, Positive-QTOF	splash10-014j-9000000000-37485ba5d1e4b146d772	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 10V, Negative-QTOF	splash10-0002-9000000000-a1565672c6279cb40dc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 20V, Negative-QTOF	splash10-0002-9000000000-d2ca5fa431fe1ddfe8d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 40V, Negative-QTOF	splash10-014i-9000000000-66f1badd4a3cbb2a48c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 10V, Positive-QTOF	splash10-014l-9000000000-bffafd7e090b1e7ae006	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 20V, Positive-QTOF	splash10-00ku-9000000000-f03c5ae1ad84267c5224	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 40V, Positive-QTOF	splash10-000i-9000000000-5bff23ef9581cf808020	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 10V, Negative-QTOF	splash10-014i-9000000000-aa96dfa89323c18d10ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 20V, Negative-QTOF	splash10-014i-9000000000-df6e1dec3ae5478c74e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Furancarboxaldehyde 40V, Negative-QTOF	splash10-00kb-9000000000-02cbdb4362802babbaba	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected and Quantified	0-202530.908 nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	21970810	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Intestinal infections	14684577	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected and Quantified	0-72471.234 nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Celiac disease
Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Enteritis
Probert CS, Jones PR, Ratcliffe NM: A novel method for rapidly diagnosing the causes of diarrhoea. Gut. 2004 Jan;53(1):58-61. [PubMed:14684577 ]
Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]