AFCDB: 1-Butanol (FDB012614)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:16 UTC

Update date

2020-09-17 15:33:57 UTC

Primary ID

FDB012614

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1-Butanol

Description

1-Butanol, also known as N-butan-1-ol or N-butyl alcohol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Thus, 1-butanol is considered to be a fatty alcohol lipid molecule. 1-Butanol is a hydrophobic molecule, poorly soluble in water, and relatively neutral. 1-Butanol is an alcohol with a 4-carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as fuel. There are four isomeric structures for butanol. The straight chain isomer with the alcohol at an internal carbon is sec-butanol or 2-butanol. The branched isomer with the alcohol at a terminal carbon is isobutanol, and the branched isomer with the alcohol at the internal carbon is tert-butanol. 1-Butanol is produced in small amounts by gut microbial fermentation through the butanoate metabolic pathway. It has been found in Bacillus, Clostridium, Escherichia, Lactobacillus, Pseudomonas, Saccharomyces, Synechococcus and Thermoanaerobacterium (http://publications.lib.chalmers.se/records/fulltext/162787.pdf) (https://ac.els-cdn.com/S0079635206800470/1-s2.0-S0079635206800470-main.pdf?_tid=1db841d3-3e7b-496f-beae-05ff16913bc6&acdnat=1550288698_645db12231ee1d15d4bb7036d31d8aad) (https://dl.uctm.edu/journal/node/j2018-4/8_17-182_p_683-696.pdf). 1-Butanol is a sweet, balsam, and fruit tasting compound. In plants, 1-Butanol is found, on average, in the highest concentration in highbush blueberries and bilberries. 1-Butanol has also been detected, but not quantified in several different foods, such as napa cabbages, wild rices, red rices, bamboo shoots, and lemon verbena.

CAS Number

71-36-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	158 g/L	ALOGPS
logP	0.84	ALOGPS
logP	0.81	ChemAxon
logS	0.33	ALOGPS
pKa (Strongest Acidic)	16.95	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.13 m³·mol⁻¹	ChemAxon
Polarizability	9.21 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

Chemical Formula

C4H10O

IUPAC name

butan-1-ol

InChI Identifier

InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3

InChI Key

LRHPLDYGYMQRHN-UHFFFAOYSA-N

Isomeric SMILES

CCCCO

Average Molecular Weight

74.1216

Monoisotopic Molecular Weight

74.073164942

Classification

Description

Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Primary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Hydrocarbon derivative
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:28885 )
alkyl alcohol (CHEBI:28885 )
Fatty alcohols (LMFA05000109 )
a primary alcohol (BUTANOL )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 64.82%; H 13.60%; O 21.59%	DFC
Melting Point	Fp -90°	DFC
Boiling Point	Bp 117.4°	DFC
Experimental Water Solubility	63.2 mg/mL at 25 oC	TEWARI,YB et al. (1982)
Experimental logP	0.88	HANSCH,C ET AL. (1995)
Experimental pKa	16.1
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d15 0.81	DFC
Refractive Index	n20D 1.3971	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-054o-9000000000-061591a78bc1cdeda799	2015-03-01	View Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-f8337e5e053a4d17e4ed	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-610cf73e0b514e180dbd	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-055f-9000000000-7e23cd40dde01cb89b6f	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-f8337e5e053a4d17e4ed	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-610cf73e0b514e180dbd	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-055f-9000000000-7e23cd40dde01cb89b6f	Spectrum
Predicted GC-MS	1-Butanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004l-9000000000-b70087d61cbf63d60bd5	Spectrum
Predicted GC-MS	1-Butanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9200000000-08a8f57a90b00db3596a	Spectrum
Predicted GC-MS	1-Butanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1-Butanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-052f-9000000000-69148177e3417cc669fd	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-052f-9000000000-7ebca2648ffd63942337	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-055f-9000000000-7e23cd40dde01cb89b6f	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-9000000000-53a465f38bad658bb673	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9145b21c5f3ae37774e0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-686e7cdc50d3fda3a0ff	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-9000000000-53a465f38bad658bb673	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9145b21c5f3ae37774e0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-686e7cdc50d3fda3a0ff	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-61d09b30d6a547d109fc	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-4d4d1c2159c658c4ee24	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-2119b542a1efb8432d12	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-61d09b30d6a547d109fc	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-4d4d1c2159c658c4ee24	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-2119b542a1efb8432d12	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-4256cf8850659dacd159	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-cb6c5eeb586ac4d5655e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-21e6cc4261bed22ecbf8	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-a749e449b2f26d0e75a2	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-b0818591ffca1f29c3ec	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-d2c85c870494f5dbfc6b	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28885

Phenol-Explorer ID

Not Available

DrugBank ID

DB02145

HMDB ID

HMDB04327

CRC / DFC (Dictionary of Food Compounds) ID

HJK39-X:HJK39-X

EAFUS ID

394

Dr. Duke ID

BUTANOL|BUTYL-ALCOHOL|N-BUTANOL|BUTAN-1-OL

BIGG ID

Not Available

KNApSAcK ID

C00035814

HET ID

1BO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

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

Descriptor	ID	Definition	Reference
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
dermatitigenic			DUKE

Enzymes

Name	Gene Name	UniProt ID
Serum paraoxonase/lactonase 3	PON3	Q15166
Serum paraoxonase/arylesterase 1	PON1	P27169
Serum paraoxonase/arylesterase 2	PON2	Q15165
Lysosomal acid phosphatase	ACP2	P11117
Sulfotransferase family cytosolic 2B member 1	SULT2B1	O00204
Alcohol dehydrogenase [NADP(+)]	AKR1A1	P14550
Beta-glucuronidase	GUSB	P08236
Plasma alpha-L-fucosidase	FUCA2	Q9BTY2
Lecithin retinol acyltransferase	LRAT	O95237
Nuclear receptor subfamily 1 group I member 3	NR1I3	Q14994
Fatty acyl-CoA reductase 2	FAR2	Q96K12
Acyl-CoA wax alcohol acyltransferase 2	AWAT2	Q6E213
Testicular acid phosphatase	ACPT	Q9BZG2
Carboxylesterase 5A	CES5A	Q6NT32
Acid phosphatase-like protein 2	ACPL2	Q8TE99
Synaptic vesicle membrane protein VAT-1 homolog-like	VAT1L	Q9HCJ6
Quinone oxidoreductase PIG3	TP53I3	Q53FA7
Synaptic vesicle membrane protein VAT-1 homolog	VAT1	Q99536
Retinol dehydrogenase 13	RDH13	Q8NBN7

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
medicine	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fruit	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
vanilla	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
medicinal	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fusel	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oil	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam	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

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

1-Butanol (FDB012614)

Structure for FDB012614 (1-Butanol)