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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-12 02:08:15 UTC

Update Date

2023-02-21 17:28:20 UTC

HMDB ID

HMDB0040575

Secondary Accession Numbers

HMDB40575

Metabolite Identification

Common Name

Butyl formate

Description

Butyl formate is a formate ester resulting from the formal condensation of formic acid with the hydroxy group of butan-1-ol. It has been found in apples, strawberries, sherry and Pamesan cheese, and it has a fruity, plum-like odour and taste. It has a role as a polar aprotic solvent, a flavouring agent and a fragrance. It derives from a butan-1-ol. Butyl formate, also known as butyl methanoate or fema 2916, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Butyl formate has been detected, but not quantified, in blackcurrants and pineapples.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Butyl methanoate	ChEBI
FEMA 2916	ChEBI
FEMA no. 2196	ChEBI
Formic acid butyl ester	ChEBI
Formic acid, butyl ester	ChEBI
N-Butyl formate	ChEBI
N-Butyl methanoate	ChEBI
Butyl methanoic acid	Generator
Formate butyl ester	Generator
Formate, butyl ester	Generator
N-Butyl formic acid	Generator
N-Butyl methanoic acid	Generator
Butyl formic acid	Generator
Butylester kyseliny mravenci	HMDB
hcoo(CH2)3ch3	HMDB

Chemical Formula

C₅H₁₀O₂

Average Molecular Weight

102.1317

Monoisotopic Molecular Weight

102.068079564

IUPAC Name

butyl formate

Traditional Name

N-butylformate

CAS Registry Number

592-84-7

SMILES

CCCCOC=O

InChI Identifier

InChI=1S/C5H10O2/c1-2-3-4-7-5-6/h5H,2-4H2,1H3

InChI Key

NMJJFJNHVMGPGM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Feces (PMID: 19167006)

Cellular substructure

Extracellular (HMDB: HMDB0040575)
Cytoplasm (HMDB: HMDB0040575)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040575)

Source

Exogenous

Exogenous (HMDB: HMDB0040575)

Food

Food (HMDB: HMDB0040575)

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)

Tropical fruit

Pineapple (FooDB: FOOD00012)

Endogenous

Plant

Plant (HMDB: HMDB0040575)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040575)

Biological role

Nutrient (HMDB: HMDB0040575)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-91.5 °C	Not Available
Boiling Point	106.10 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	7.56 mg/mL at 27 °C	Not Available
LogP	1.396 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	20.4 g/L	ALOGPS
logP	1.53	ALOGPS
logP	1.2	ChemAxon
logS	-0.7	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	26.8 m³·mol⁻¹	ChemAxon
Polarizability	11.33 Å³	ChemAxon
Number of Rings	0	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]+	119.858	31661259
DarkChem	[M-H]-	115.636	31661259
DeepCCS	[M+H]+	129.518	30932474
DeepCCS	[M-H]-	127.623	30932474
DeepCCS	[M-2H]-	163.316	30932474
DeepCCS	[M+Na]+	137.806	30932474
AllCCS	[M+H]+	125.6	32859911
AllCCS	[M+H-H2O]+	121.3	32859911
AllCCS	[M+NH4]+	129.6	32859911
AllCCS	[M+Na]+	130.8	32859911
AllCCS	[M-H]-	128.7	32859911
AllCCS	[M+Na-2H]-	132.6	32859911
AllCCS	[M+HCOO]-	136.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.77 minutes	32390414
Predicted by Siyang on May 30, 2022	11.149 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1448.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	379.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	138.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	259.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	162.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	401.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	480.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	873.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	318.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1055.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	454.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	307.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	79.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butyl formate	CCCCOC=O	1007.2	Standard polar	33892256
Butyl formate	CCCCOC=O	689.1	Standard non polar	33892256
Butyl formate	CCCCOC=O	793.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Butyl formate EI-B (Non-derivatized)	splash10-0a4l-9000000000-e7e1458477b7320af8a0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl formate EI-B (Non-derivatized)	splash10-0a6u-9000000000-69a6b7dc8e0c0a8fb002	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl formate EI-B (Non-derivatized)	splash10-0a4l-9000000000-e7e1458477b7320af8a0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl formate EI-B (Non-derivatized)	splash10-0a6u-9000000000-69a6b7dc8e0c0a8fb002	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl formate GC-MS (Non-derivatized) - 70eV, Positive	splash10-056u-9000000000-c8b554b36cf9d4a1bc00	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl formate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a6u-9000000000-179d2d59f5490a925ec2	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 10V, Positive-QTOF	splash10-0zfr-6900000000-69526b55b3e3aa7735b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 20V, Positive-QTOF	splash10-0a4i-9100000000-4303f610cc775006a83c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 40V, Positive-QTOF	splash10-0a4i-9000000000-3c131ddd792691766350	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 10V, Negative-QTOF	splash10-0udi-2900000000-21ee9f10534dad5ce3ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 20V, Negative-QTOF	splash10-0udl-9600000000-fb3a67b3f780201eeabc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 40V, Negative-QTOF	splash10-0006-9000000000-5189f4a92c86ecd0092a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 10V, Negative-QTOF	splash10-0uk9-8900000000-1c987cadff7b021224ea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 20V, Negative-QTOF	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 40V, Negative-QTOF	splash10-0006-9000000000-4c6d0336968575d2ae9d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 10V, Positive-QTOF	splash10-0a4i-9000000000-638fcdcccda1a62f9c55	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 20V, Positive-QTOF	splash10-0a4i-9000000000-8358265d2ce5d040c945	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl formate 40V, Positive-QTOF	splash10-0a4l-9000000000-fbfb691448b8325098c7	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

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	19167006	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020353

KNApSAcK ID

Not Available

Chemspider ID

11125

KEGG Compound ID

Not Available

BioCyc ID

CPD-18956

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11614

PDB ID

Not Available

ChEBI ID

88514

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1013381

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Butyl formate (HMDB0040575)

MOL for HMDB0040575 (Butyl formate)

3D MOL for HMDB0040575 (Butyl formate)

3D SDF for HMDB0040575 (Butyl formate)

3D-SDF for HMDB0040575 (Butyl formate)

PDB for HMDB0040575 (Butyl formate)

3D PDB for HMDB0040575 (Butyl formate)

SMILES for HMDB0040575 (Butyl formate)

INCHI for HMDB0040575 (Butyl formate)

Structure for HMDB0040575 (Butyl formate)

3D Structure for HMDB0040575 (Butyl formate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra