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2-methyl-1-butanol

Chemical Structure

General Material Information

Preferred name 2-methyl-1-butanol
Trivial Name 2-Methyl-1-butanol
Short Description 2-methylbutan-1-ol
Formula C5 H12 O
CAS Number 137-32-6
Deleted CAS Number 34713-94-5
FEMA Number 3998
Flavis Number 2.076
ECHA Number 205-289-9
FDA UNII 7VTJ239ASU
Nikkaji Number J2.022B
Beilstein Number 1718810
MDL MFCD00004743
COE Number 2346
xLogP3-AA 1.20 (est)
NMR Predictor External link
JECFA Food Flavoring 1199 (+/-)-2-methyl-1-butanol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 137-32-6 ; 2-METHYL-1-BUTANOL
Synonyms
  • butan-1-ol, 2-methyl-
  • 1-butanol, 2-methyl-
  • 1-butanol, 2-methyl-, (±)-
  • di-sec-butyl carbinol
  • 2-methyl butan-1-ol
  • 2-methyl butanol
  • 2-methyl butyl alcohol
  • 2-methyl butyl alcohol natural
  • (+/-)-2-methyl-1-butanol
  • DL-2-methyl-1-butanol
  • 2-methyl-1-butanol natural
  • methyl-2-butan-1-ol
  • methyl-2-butanol-1
  • 2-methyl-N-butanol
  • (1)-2-methylbutan-1-ol
  • 2-methylbutan-1-ol
  • 2-methylbutanol
  • nat.L-2-methylbutanol
  • 2-methylbutyl alcohol
  • 2-methylbutan-1-ol
  • 1-Butanol, 2-methyl-
  • sec-Butylcarbinol
  • Primary active amyl alcohol
  • Active amyl alcohol
  • Active primary amyl alcohol
  • 2-Methyl-n-butanol
  • 2-Methylbutyl alcohol
  • (±)-2-Methyl-1-butanol
  • NSC 8431

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Perfumer & Flavorists Start search
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Literature & References

Leffingwell:Chirality or Article
2-methylbutan-1-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:137-32-6
Pubchem (cid):8723
Pubchem (sid):134973580
Flavornet:137-32-6
Pherobase:View
Publications by US Patents
7,932,293 - Aldehyde compositions and methods for providing fragrance containing the same
Publications by PubMed
Engineering Corynebacterium crenatum to produce higher alcohols for biofuel using hydrolysates of duckweed (Landoltia punctata) as feedstock.
Volatile Profiles of Members of the USDA Geneva Malus Core Collection: Utility in Evaluation of a Hypothesized Biosynthetic Pathway for Esters Derived from 2-Methylbutanoate and 2-Methylbutan-1-ol.
The dynamics of the HS/SPME-GC/MS as a tool to assess the spoilage of minced beef stored under different packaging and temperature conditions.
High-quality Italian rice cultivars: chemical indices of ageing and aroma quality.
A new hemiterpene glycoside from the ripe tomatoes.
The exometabolome of Clostridium thermocellum reveals overflow metabolism at high cellulose loading.
Differential field responses of the little fire ant, Wasmannia auropunctata (Roger), to alarm pheromone enantiomers.
Production of volatiles in fresh-cut apple: effect of applying alginate coatings containing linoleic acid or isoleucine.
Metabolic engineering of microorganisms for the production of higher alcohols.
Analysis of volatile components of cape gooseberry (Physalis peruviana L.) grown in Turkey by HS-SPME and GC-MS.
Tumor necrosis factor-related apoptosis-inducing ligand regulates hallmark features of airways remodeling in allergic airways disease.
Salmeterol attenuates chemotactic responses in rhinovirus-induced exacerbation of allergic airways disease by modulating protein phosphatase 2A.
Effect of high oxygen and high carbon dioxide atmosphere packaging on the microbial spoilage and shelf-life of fresh-cut honeydew melon.
Characterization of volatile components in makgeolli, a traditional Korean rice wine, with or without pasteurization, during storage.
Widely applicable synthesis of enantiomerically pure tertiary alkyl-containing 1-alkanols by zirconium-catalyzed asymmetric carboalumination of alkenes and palladium- or copper-catalyzed cross-coupling.
Furry pet allergens, fungal DNA and microbial volatile organic compounds (MVOCs) in the commercial aircraft cabin environment.
A survey of insect assemblages responding to volatiles from a ubiquitous fungus in an agricultural landscape.
Muscodor albus volatiles control toxigenic fungi under Controlled Atmosphere (CA) storage conditions.
Characterisation of tequila according to their major volatile composition using multilayer perceptron neural networks.
Control over the color transition behavior of polydiacetylene vesicles using different alcohols.
Volatile organic compounds derived from 2-keto-acid decarboxylase in Microcystis aeruginosa.
Evaluation of fast volatile analysis for detection of Botrytis cinerea infections in strawberry.
Unusual dielectric strength of Debye relaxation in monohydroxy alcohols upon mixing.
Thermal decomposition of 1-pentanol and its isomers: a theoretical study.
Determination of volatile compounds in wine by gas chromatography-flame ionization detection: comparison between the U.S. Environmental Protection Agency 3sigma approach and Hubaux-Vos calculation of detection limits using ordinary and bivariate least squares.
Volatile emissions from an epiphytic fungus are semiochemicals for eusocial wasps.
The effect of alcohol structures on the interaction mode with the hexameric capsule of resorcin[4]arene.
Quorum sensing activity in Ophiostoma ulmi: effects of fusel oils and branched chain amino acids on yeast-mycelial dimorphism.
Sequencing and characterizing odorant receptors of the cerambycid beetle Megacyllene caryae.
A novel synthetic odorant blend for trapping of malaria and other African mosquito species.
Optimization of fermentation conditions for production of the jabuticaba (Myrciaria cauliflora) spirit using the response surface methodology.
Production of volatile organic compounds by mycobacteria.
Branched-chain higher alcohols.
Current knowledge on isobutanol production with Escherichia coli, Bacillus subtilis and Corynebacterium glutamicum.
Development of a headspace trap HRGC/MS method for the assessment of the relevance of certain aroma compounds on the sensorial characteristics of commercial apple juice.
Engineering Bacillus subtilis for isobutanol production by heterologous Ehrlich pathway construction and the biosynthetic 2-ketoisovalerate precursor pathway overexpression.
Outlining a future for non-Saccharomyces yeasts: selection of putative spoilage wine strains to be used in association with Saccharomyces cerevisiae for grape juice fermentation.
Microbial ethanol production: experimental study and multivariate evaluation.
Time-resolved gas-phase kinetic, quantum chemical, and RRKM studies of reactions of silylene with alcohols.
Evolution, genomic analysis, and reconstruction of isobutanol tolerance in Escherichia coli.
Use of the valine biosynthetic pathway to convert glucose into isobutanol.
Relationship between changes in the total concentration of acetic acid bacteria and major volatile compounds during the acetic acid fermentation of white wine.
Analytical aspects of cyanobacterial volatile organic compounds for investigation of their production behavior.
The effect of raw material contamination with mycotoxins on the composition of alcoholic fermentation volatile by-products in raw spirits.
Identification of a pheromone regulating caste differentiation in termites.
Engineering Corynebacterium glutamicum for isobutanol production.
Influence of pre-cure freezing on the profile of volatile compounds during the processing of Iberian hams.
New syntheses of 1,7-dimethylnonyl propanoate, the western corn rootworm pheromone, in four different ways via cross metathesis, alkylation and coupling reactions.
Aromatic potential of botrytized white wine grapes: identification and quantification of new cysteine-S-conjugate flavor precursors.
Predicting the adsorption of second generation biofuels by polymeric resins with applications for in situ product recovery (ISPR).
Pentanol isomer synthesis in engineered microorganisms.
Volatile antimicrobials from Muscodor crispans, a novel endophytic fungus.
The use of headspace solid phase microextraction for the characterization of volatile compounds in olive oil matrices.
Production of 2-methyl-1-butanol in engineered Escherichia coli.
Filament formation in Saccharomyces cerevisiae--a review.
Microbial volatile organic compounds in the air of moldy and mold-free indoor environments.
Detection of fungal development in closed spaces through the determination of specific chemical targets.
Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels.
Potential of the volatile-producing fungus Muscodor albus for control of building molds.
Genetic diversity of volatile components in Xinjiang Wild Apple (Malus sieversii).
Using generic pheromone lures to expedite identification of aggregation pheromones for the cerambycid beetles Xylotrechus nauticus, Phymatodes lecontei, and Neoclytus modestus modestus.
Development of synthetic food-related attractant for Carpophilus davidsoni and its effectiveness in the stone fruit orchards in southern Australia.
GC-MS SPME profiling of rhizobacterial volatiles reveals prospective inducers of growth promotion and induced systemic resistance in plants.
Metabolite production of yeasts on a strawberry-agar during storage at 7 degrees C in air and low oxygen atmosphere.
Production of volatile compounds by Rhizopus oligosporus during soybean and barley tempeh fermentation.
Volatile metabolite production of spoilage micro-organisms on a mixed-lettuce agar during storage at 7 degrees C in air and low oxygen atmosphere.
Ideal mixing behavior of the debye process in supercooled monohydroxy alcohols.
Dynamics of glass-forming liquids. IX. Structural versus dielectric relaxation in monohydroxy alcohols.
Dynamics of glass-forming liquids. VIII. Dielectric signature of probe rotation and bulk dynamics in branched alkanes.
Rapid identification of microbial VOCs from tobacco molds using closed-loop stripping and gas chromatography/time-of-flight mass spectrometry.
Growth and production of volatiles by Staphylococcus carnosus in dry sausages: Influence of inoculation level and ripening time.
An efficient and general route to reduced polypropionates via Zr-catalyzed asymmetric CC bond formation.
Effects of including silage in the diet on volatile compound profiles in Montasio cheese and their modification during ripening.
Higher-alcohols biorefinery: improvement of catalyst for ethanol conversion.
Volatiles in a sausage surface model-influence of Penicillium nalgiovense, Pediococcus pentosaceus, ascorbate, nitrate and temperature.
Changes in the order of elution of some organic compounds in high-resolution gas chromatography on polar columns depending on the injection method and water content in the sample.
Determination of major compounds in sweet wines by headspace solid-phase microextraction and gas chromatography.
Microbiological and fermentation characteristics of togwa, a Tanzanian fermented food.
Aroma active components in aqueous kiwi fruit essence and kiwi fruit puree by GC-MS and multidimensional GC/GC-O.
Growth and aroma production by Staphylococcus xylosus, S. carnosus and S. equorum--a comparative study in model systems.
Investigations of aroma volatile biosynthesis under anoxic conditions and in different tissues of "Redchief Delicious" apple fruit (Malus domestica Borkh.).
Volatile metabolites from actinomycetes.
Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor.
Significance of volatile compounds produced by spoilage bacteria in vacuum-packed cold-smoked salmon (Salmo salar) analyzed by GC-MS and multivariate regression.
Effect of carbohydrate substrate on fermentation by kefir yeast supported on delignified cellulosic materials.
Trapping social wasps (Hymenoptera: Vespidae) with acetic acid and saturated short chain alcohols.
Characterisation of whiskeys using solid-phase microextraction with gas chromatography-mass spectrometry.
Volatiles from Fusarium verticillioides (Sacc.) nirenb. and their attractiveness to nitidulid beetles.
Utilization of fluorescein sodium salt for the indirect fluorimetric detection in micellar electrokinetic chromatography.
Evaluation of skin damage caused by percutaneous absorption enhancers using fractal analysis.
Gas chromatographic determination of volatile congeners in spirit drinks: interlaboratory study.
Qualitative identification of volatile metabolites from two fungi and three bacteria species cultivated on two media.
Pyruvate decarboxylase catalyzes decarboxylation of branched-chain 2-oxo acids but is not essential for fusel alcohol production by Saccharomyces cerevisiae.
Prediction of Phase Behavior in Microemulsion Systems Using Artificial Neural Networks
Identification of volatile metabolites from five fungal species cultivated on two media.
Determination of alpha-alkyl-alpha-amino acids and alpha-amino alcohols by chiral-phase capillary gas chromatography and reverse-phase high-performance liquid chromatography.
By-product inhibition effects on ethanolic fermentation by Saccharomyces cerevisiae.
Stereospecific reductions of 2-en-1-ols catalyzed by Clostridium kluyveri.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
FooDB:FDB012107
YMDB (Yeast Metabolome Database):YMDB00567
Export Tariff Code:2905.19.9090
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
exists in commerce largely as d-amyl alcohol.

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 88.149841308594
Specific gravity @ 25 °C
Pounds per Gallon 6.782 to 6.823
Refractive Index 1.409 to 1.412 @ 20 °C
Boiling Point 128 to 130°C @ 760 mm Hg
Acid Value 1 max KOH/g
Vapor Pressure 4.76 mmHg @ 25 °C
Vapor Density 3
Flash Point TCC Value 43.33 °C TCC
logP (o/w) 1.29
Solubility
alcohol Yes
water, 3.22e+004 mg/L @ 25 °C (est) Yes
water, 2.97E+04 mg/L @ 25 °C (exp) Yes

Organoleptic Properties

Odor Type: Ethereal
ethereal, fusel, alcoholic, fatty, greasy, winey, whiskey, leathery, cocoa
Odor strength medium
Substantivity < 1 hour(s) at 100.00 %
Luebke, William tgsc, (2021) At 100.00 %. ethereal fusel alcoholic fatty greasy winey whiskey leathery cocoa
Flavor Type: Ethereal
ethereal, alcoholic, fatty, greasy, cocoa, whiskey, fusel, leathery
Luebke, William tgsc, (2021) Ethereal alcoholic fatty greasy cocoa whiskey fusel leathery

Occurrences

Potential Uses

Applications
Flavoring purposes Tropical
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable.
R 20 - Harmful by inhalation.
R 37 - Irritating to respiratory system.
R 66 - Repeated exposure may cause skin dryness or cracking.
S 16 - Keep away from sources of ignition - No Smoking.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
S 46 - If swallowed, seek medical advice immediately and show this container or label.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
parenteral-frog LDLo 2448 mg/kg
PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 50, Pg. 296, 1935.

intraperitoneal-rat LDLo 1900 mg/kg
Journal of Industrial Hygiene and Toxicology. Vol. 27, Pg. 1, 1945.

Dermal Toxicity:
skin-rabbit LD50 3540 ul/kg
American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 2-methyl-1-butanol usage levels up to:
1.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.73 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 35.00 (μg/capita/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 20. Update in publication number(s): 29
Click here to view publication 20
average usual ppmaverage maximum ppm
baked goods: 2.000009.00000
beverages(nonalcoholic): 0.100002.00000
beverages(alcoholic): 400.000001100.00000
breakfast cereal: --
cheese: --
chewing gum: 2.0000015.00000
condiments / relishes: --
confectionery froastings: 0.300002.00000
egg products: 0.300002.00000
fats / oils: 0.5000015.00000
fish products: --
frozen dairy: 1.500008.00000
fruit ices: 0.800005.00000
gelatins / puddings: 0.200002.00000
granulated sugar: --
gravies: 0.300002.50000
hard candy: 0.300003.00000
imitation dairy: --
instant coffee / tea: 0.100001.00000
jams / jellies: 0.400004.00000
meat products: --
milk products: 0.100001.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 0.300002.50000
snack foods: 0.400004.00000
soft candy: 0.400004.00000
soups: 0.200002.00000
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 1, Revision 1 (FGE.01Rev 1): Branched-chain aliphatic saturated aldehydes, carboxylic acids and related esters of primary alcohols and branched-chain carboxylic acids from chemical groups 1 and 2 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission
View page or View pdf

Flavouring Group Evaluation 3, Revision 1 (FGE.03Rev1): Acetals of branched- and straight-chain aliphatic saturated primary alcohols and branched- and straight-chain saturated or unsaturated aldehydes, an ester of a hemiacetal and an orthoester of formic acid, from chemical groups 1, 2 & 4 Commission Regulation (EC) No 1565/2000 of 18 July 2000) [1] - Scientific Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)on a request from the Commission
View page or View pdf

Flavouring Group Evaluation 5, Revision 1 (FGE.05Rev1):Esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids from chemical groups 1, 2, and 5 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) [1] - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 2, Revision 1 (FGE.02) : Branched- and straight-chain aliphatic saturated primary alcohols and related esters of primary alcohols and straight-chain carboxylic acids and one straight-chain aldehyde from chemical groups 1 and 2 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 20, Revision 1 (FGE.20Rev1): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids and related esters from chemical group 23
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 20, Revision 2 (FGE.20Rev2): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf

Flavouring Group Evaluation 72 (FGE.72): Consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids, and related esters evaluated by the JECFA (61st meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids. Esters of these and straight-chain aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2 (2010)
View page or View pdf

Flavouring Group Evaluation 5, Revision 2 (FGE.05Rev2): Branched- and straight-chain unsaturated carboxylic acids and esters of these with aliphatic saturated alcohols from chemical groups 1, 2, 3 and 5
View page or View pdf

Flavouring Group Evaluation 01 Rev2 (FGE.01 Rev2): Branched-chain aliphatic saturated aldehydes, carboxylic acids and related esters of primary alcohols and branched-chain carboxylic acids from chemical groups 1 and 2
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 20, Revision 3(FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 72, Revision 1 (FGE.72Rev1): Consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids, and related esters evaluated by the JECFA (61st meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids, esters of these and straight-chain aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 72, Revision 2 (FGE.72Rev2): consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids and related esters evaluated by JECFA (61st, 68th and 69th meetings) and structurally related to flavouring substances in FGE.05Rev3
View page or View pdf

EPI System: View
NIOSH International Chemical Safety Cards:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):137-32-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :8723
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1105
WGK Germany:1
2-methylbutan-1-ol
Chemidplus:0000137326
RTECS:137-32-6