ISOAMYL ALCOHOL

Isoamyl alcohol = Isopentyl alcohol

CAS Number: 123-51-3
EC Number: 204-633-5
Molecular Weight: 88.15

WHAT IS ISOAMYL ALCOHOL?
Isoamyl alcohol is a speciality solvent that finds extensive use for flavours and fragrances and is used in the production of many synthetic flavours. 
Isoamyl alcohols relatively low eco-tox profile finds Isoamyl alcohol use growing in other areas.

Isoamyl alcohol is a principal ingredient in the production of banana oil, a natural ester used in the flavoring industry. 
Isoamyl alcohol is also used as an antifoaming agent in the Chloroform: Isomyl Alcohol reagent.
Isoamyl alcohol is a colorless, clear liquid with the chemical formula (CH3)2CHCH2CH2OH and the CAS # 123-51-3. 
The nontoxic compound has a mild, choking disagreeable odor. 

Isoamyl alcohol is less dense than water, soluble in water, and floats on water. 
Isoamyl alcohols main use in industry is as a food additive and flavoring agent. 
Isoamyl alcohol is manufactured from light petroleum by fractional distillation.

Isoamyl alcohol is a colorless liquid with the formula C5H12O, specifically (H3C–)2CH–CH2–CH2–OH. 
Isoamyl alcohol is one of several isomers of amyl alcohol (pentanol). 
Isoamyl alcohol is also known as isopentyl alcohol, Isopentanol, or (in the IUPAC recommended nomenclature) 3-methyl-butan-1-ol. 
An obsolete name for Isoamyl alcohol was isobutyl carbinol. 

CAS Number: 123-51-3
Synonyms: 3-Methy-1-butanol, Isopentyl alcohol
Physical State: Colourless liquid
Odour: Pear drops, ester
Viscosity: 7.2mPas (at 21°C)
Solubility in water: 28g/L
Boiling Point: 131-132°C

Applications: The main applications of Isoamyl Alcohol are:
– the manufacturing of paints and varnishes, to produce isoamyl acetate;
– the manufacturing of plasticizers for the production of DIAP (DiisoAmyl phthalate);
– the manufacturing of perfumes, for the recovery of oils and essences;
– the synthesis of fragrances and aromas;
– the production of isoamyl salicylate, applied widely in soaps and cosmetic fragrances;
– the purification of phosphoric acid, acting as an extraction solvent.
– the production of Xanthates (mining industry)

Isoamyl alcohol is an ingredient in the production of banana oil, an ester found in nature and also produced as a flavouring in industry. 
Isoamyl alcohol is a common fusel alcohol, produced as a major by-product of ethanol fermentation.

Occurrence
Isoamyl alcohol is one of the components of the aroma of Tuber melanosporum, the black truffle.
The compound has also been identified as a chemical in the pheromone used by hornets to attract other members of the hive to attack. 
Isoamyl acetate is a component of the natural aroma of bananas, especially the Gros Michel variety.

Extraction from fusel oil
Isoamyl alcohol can be separated from fusel oil by either of two methods: shaking with strong brine solution and separating the oily layer from the brine layer; distilling it and collecting the fraction that boils between 125 and 140 °C. 
Further purification is possible with this procedure: shaking the product with hot limewater, separating the oily layer, drying the product with calcium chloride, and distilling it, collecting the fraction boiling between 128 and 132 °C.

Synthesis
Isoamyl alcohol can be synthesized by condensation of isobutene and formaldehyde which produces isoprenol and hydrogenation. 
Isoamyl alcohol is a colourless liquid of density 0.8247 g/cm3 (0 °C), boiling at 131.6 °C, slightly soluble in water, and easily dissolved in organic solvents. 
Isoamyl alcohol has a characteristic strong smell and a sharp burning taste. 
Amyl alcohol has an oral LD50 of 200 mg/kg in mice, suggesting that Isoamyl alcohol is significantly more toxic than ethanol. 
On passing the vapour through a red-hot tube, Isoamyl alcohol decomposes into acetylene, ethylene, propylene, and other compounds. 
Isoamyl alcohol is oxidized by chromic acid to isovaleraldehyde, and Isoamyl alcohol forms addition compounds crystals with calcium chloride and tin(IV) chloride.

Uses of Isoamyl alcohol
Besides Isoamyl alcohols use in the synthesis of banana oil, isoamyl alcohol is also an ingredient of Kovac's reagent, used for the bacterial diagnostic indole test.
Isoamyl alcohol is also used as an antifoaming agent in the chloroform isoamyl alcohol reagent.
Isoamyl alcohol is used in a phenol–chloroform extraction mixed with the chloroform to further inhibit RNase activity and prevent solubility of RNAs with long tracts of poly-adenine.

General description
Isoamyl alcohol is a cyanobacterial volatile organic compound that has been identified as one of the main aroma/flavor constituents in banana fruit, karanda fruits and in whey spirit.

Isoamyl alcohol, also known as isopentyl alcohol or 3-methylbutanol, 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, Isoamyl alcohol is considered to be a fatty alcohol. 
Isoamyl alcohol exists in all eukaryotes, ranging from yeast to plants to humans. 
In yeast, Isoamyl alcohol is involved in the metabolic pathway called the leucine degradation pathway. 
Based on a literature review a significant number of articles have been published on Isoamyl alcohol.

Synonym(s): Isopentyl alcohol, Isoamyl alcohol, 3-Methyl-1-butanol
Linear Formula: (CH3)2CHCH2CH2OH
CAS Number: 123-51-3
Molecular Weight: 88.15
FEMA Number: 2057
Beilstein/REAXYS Number: 1718835
EC Number: 204-633-5
Council of Europe no.: 51
MDL number: MFCD00002934
PubChem Substance ID: 24900824
Flavis number: 2.003
NACRES: NA.21

ISOAMYL ALCOHOL
Isoamyl alcohol is one of the flavour and fragrance chemicals produced by Chemoxy. 
Isoamyl alcohol is a speciality solvent often noted for its distinctive odour – which smells like pear drops.

PRODUCT IDENTIFICATION
Product Name: Isoamyl Alcohol
Empirical Formula: C5H12O

APPLICATIONS
Isoamyl alcohol is used as a solvent for the preparation of synthetic fruit flavours, such as apricot, banana, cheery, greengage, malt, orange, plum and whiskey flavours, and is a raw material in the production of synthetic banana oil. 
Isoamyl alcohol is one of the components of the aroma of the black truffle. 
Isoamyl alcohol is also used for estimation of fat in milk and milk products.

A derivative of Isoamyl alcohol, the p-methoxycinnamate is used as a UV absorber in some cosmetic formulations, and the product itself finds application as a cosmetic flavouring and in perfume.
If you are interested in isoamyl alcohol you may also like to visit the Isoamyl acetate page. 
Please feel free to contact the experts at Chemoxy if you have a question about the properties and applications of Isoamyl alcohol.

Preferred IUPAC name
3-Methylbutan-1-ol

Other names
3-Methyl-1-butanol
Isopentyl alcohol
Isoamyl alcohol
Isobutylcarbinol

CAS Number: 123-51-3  
CHEBI: 15837 
ChEMBL: ChEMBL372396 
ChemSpider: 29000  
DrugBank: DB02296 
ECHA InfoCard:    100.004.213  
KEGG: C07328  
PubChem CID: 31260
UNII: DEM9NIT1J4  
CompTox Dashboard (EPA): DTXSID3025469

Application Notes
Isoamy alcohol is routinely used in molecular biology, especially in the purification of DNA. 
Isoamyl alcohol is widely used in conjunction with phenol and chloroform (25:24:1 phenol : chloroform : isoamyl alcohol) for the removal of proteins from the nucleic acid solutions by extraction. 
Isoamyl alcohol is added to the phenol solution to help inhibit RNase activity and to help prevent the solubilization in the phenol phase of long RNA molecules with long poly(A) portions. 
Isoamyl alcohol will also help in reducing the foaming during the extraction process.
Isoamyl alcohol is also used in the extraction of ethidium bromide from DNA solutions and in the radiolabeling of RNA transcripts in nuclei that have been isolated from tissue. 
Isoamyl alcohol has various miscellaneous uses which include HPLC analysis of various pharmaceuticals and metabolites, analysis of oxidized and reduced pyridine nucleotides and adenylates in organic phenol extracts from mitochondria, isolation of mRNA from a thermophilic cyanobacterium, Solvent for fats, resins, alkaloids, Manufacturing isoamyl (amyl) compounds, isovaleric acid, mercury fulminate, pyroxylin, artificial silk, lacquers, smokeless powders, for dehydrating celloidin solutions, for determining fat in milk etc.

Chemical formula: C5H12O
Molar mass: 88.148 g/mol
Appearance: Clear, colorless liquid
Density: 0.8104 g/cm3 at 20 °C
Melting point: −117 °C (−179 °F; 156 K)
Boiling point: 131.1 °C (268.0 °F; 404.2 K)
Solubility in water: Slightly soluble, 28 g/L
Solubility: Very soluble in acetone, diethyl ether, ethanol
Vapor pressure: 28 mmHg (20 °C) 
Magnetic susceptibility (χ): −68.96·10−6 cm3/mol
Viscosity: 3.692 mPa·s

Isoamyl alcohol (Isopentyl Alcohol, 3-Methylbutanol): Isoamyl alcohol is designated as Molecular Biology grade and is suitable for use in nucleic acid purification. 
3-Methyl-1-butanol, commonly called isoamyl alcohol,is routinely used in molecular biology, notably in the purification of DNA. 
Isoamyl alcohol is widely used in conjunction with phenol and chloroform, for the removal of proteins from the nucleic acid solutions by extraction. 
The addition of chloroform and isoamyl alcohol in the extraction protocol deals with two issues that the use of phenol alone does not completely address: Isoamyl alcohol helps to inhibit RNase activity, which phenol does not completely inhibit,Isoamyl alcohol helps to prevent the solubilization in the phenol phase of long RNA molecules with long poly(A) portions. 
In addition, isoamyl alcohol reduces foaming during the extraction process. 
Isoamyl alcohol may also be used in the extraction of ethidium bromide from DNA solutions and in the radiolabeling of RNA transcripts in nuclei that have been isolated from tissue. 
Isoamyl alcohol is often used in the HPLC analysis of various pharmaceuticals and metabolites. 

Isoamyl alcohol has been used in the analysis of oxidized and reduced pyridine nucleotides and adenylates in organic phenol extracts from mitochondria. 
A phenol:chloroform:isoamyl alcohol procedure for the extraction of chloroplast DNA that avoids density gradient differential centrifugation has been published. 
A protocol for the isolation of mRNA from a thermophilic cyanobacterium that incorporates a phenol:chloroform:isoamyl alcohol mixture has been described.

Isoamyl alcohol, also known as isoamyl alcohol or 3-methylbutanol, 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, Isoamyl alcohol is considered to be a fatty alcohol lipid molecule. 
Isoamyl alcohol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 
Isoamyl alcohol exists in all eukaryotes, ranging from yeast to humans. 
Isoamyl alcohol is an alcoholic, banana, and burnt tasting compound. 

Isoamyl alcohol is found, on average, in the highest concentration within milk (cow). 
Isoamyl alcohol has also been detected, but not quantified, in several different foods, such as chinese cinnamons, grapefruits, walnuts, wild leeks, and spearmints. 
This could make Isoamyl alcohol a potential biomarker for the consumption of these foods. Isoamyl alcohol is one of several isomers of amyl alcohol.
Isoamyl alcohol is the major higher chain alcohol in alcoholic beverages and is present in cider, mead, beer, wine, and spirits to varying degrees, being obtained by the fermentation of starches. 
Isoamyl alcohol, with regard to humans, has been found to be associated with the diseases such as ulcerative colitis; Isoamyl alcohol has also been linked to the inborn metabolic disorder celiac disease.

Formula: C5H12O / (CH3)2CHCH2CH2OH
Molecular mass: 88.2
Boiling point: 132°C
Melting point: -117°C
Relative density (water = 1): 0.8
Solubility in water, g/100ml: 2.5 (moderate)
Vapour pressure, kPa at 20°C: 0.4
Relative vapour density (air = 1): 3.0
Relative density of the vapour/air-mixture at 20°C (air = 1): 1.01
Flash point: 42°C c.c.
Auto-ignition temperature: 340°C
Explosive limits, vol% in air: 1.2-10.5 (at 100°C)
Octanol/water partition coefficient as log Pow: 1.28
Viscosity: 4.67 mm²/s at 25°C 

Isoamyl Alcohol is used as a solvent and as a raw material for acetate esters, plasticizers and lubricant components. 
Can be the effective cosurfactant used in DNA extraction or for preparation stable microemulsions. 
Isoamyl alcohol is specifically flavored for flavoring and perfume use. 
Isoamyl alcohol is the intermediate for thiophene and acetate manufacture. 
Isoamyl alcohol (IA) is colorless to pale yellow, clear liquid with characteristic, disagreeable alcohol-like odor. 

Soluble in alcohol and ether but slightly soluble in water. 
Stable under ordinary conditions of use and storage. 
Heat contributes to instability. 
Flammable. 
Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides. 
Reacts with reducing agents.   
Specifications: 
Density: 810.40 kg/m³ 
Formula: C5H12O 
Molar mass: 88.148 g/mol 
Melting point: -117.2 °C

Isoamyl Alcohol (at a minimum purity of 99%), is a mixture of isomers 3-methyl, 1-butanol and 2-methyl , 1-butanol, with a preponderance of the first (aproximately 85%). 
The raw material used by PETROM in the production of Isoamyl Alcohol is fusel oil, which in turn is a byproduct of the distilling of ethyl alcohol (ethanol).
Isoamyl alcohol (also known as isopentyl alcohol) is a clear, colorless alcohol with the formula (CH3)2CHCH2CH2OH. 
Isoamyl alcohol is one of several isomers of amyl alcohol. 
Isoamyl alcohol is a main ingredient in the production of banana oil, an ester found in nature and also produced as a flavouring in industry. 
Isoamyl alcohol's also the main ingredient of Kovac's reagent, used for the bacterial diagnostic indole test.

Isoamyl alcohol is also used as an antifoaming agent in the Chloroform: Isomyl Alcohol reagent.
Isoamyl alcohol is used in a Phenol-chloroform extraction mixed with the chloroform to further inhibit RNase activity and prevent solubility of RNAs with long tracts of poly-adenine. 
Isoamyl alcohol is one of the components of the aroma of Tuber melanosporum, the black truffle. 
Isoamyl alcohol has been identified as a chemical in the pheromone used by hornets to attract other members of the hive to attack.

Isoamyl alcohol is a specialty solvent that finds extensive use for flavours and fragrances and is used in the production of many synthetic flavours. 
Isoamyl alcohols relatively low eco-tox profile finds Isoamyl alcohol use growing in other areas. 
Isoamyl alcohol is used as a solvent for the preparation of synthetic fruit flavours, such as apricot, banana, cheery, greengage, malt, orange, plum and whiskey flavours, and is a raw material in the production of synthetic banana oil. 
Isoamyl alcohol is one of the components of the aroma of the black truffle. 
Isoamyl alcohols blend of properties makes Isoamyl alcohol suitable for use as a foam suppressant, affecting the surface tension of micro-emulsions and causing foam breaking.

The mechanism of the formation of isoamyl alcohol during alcoholic fermentation was studied by using radioactive leucine and isovaleraldehyde and determining the percentage of isoamyl alcohol derived from these precursors. 
The results partially confirm previous work in this field, but also indicate that the ultimate precursor of isoamyl alcohol is to be found in the fermentable sugar.

Other names: Isopentyl alcohol; Fermentation amyl alcohol; Fusel Oil; Isoamyl alcohol
Isoamylol; Isobutyl carbinol; Isoamyl alcohol; 2-Methyl-4-butanol; 3-Methyl-1-butanol
3-Methylbutanol; Alcool amilico; Alcool isoamylique; Amylowy alkohol; iso-amylalkohol
3-Methylbutan-1-ol; 3-Metil-butanolo; Isoamyl alcohol, primary; Butanol, 3-methyl-
Butan-1-ol, 3-methyl; i-Amyl alcohol; Isopentan-1-ol; Methyl-3-butan-1-ol
NSC 1029; UN 1105; 3-methylbutanoI; Isoamyl alcohol (3-methyl butanol)

Isoamyl alcohol is the main ingredient of Kovac’s Reagent used for the bacterial diagnostic Indole Test.
Isoamyl alcohols blend of properties makes it suitable for use as a foam suppressant, affecting the surface tension of micro-emulsions and causing foam breaking.
As a solvent, Isoamyl alcohol is finding increasing use in a wide number of industrial applications. 

autoignition temp.: 644 °F
expl. lim.: 1.2-9 %, 100 °F
refractive index: n20/D 1.406 (lit.)
pH: 5.6 (20 °C, 25 g/L)
bp: 130 °C (lit.)
mp: −117 °C (lit.)
density: 0.809 g/mL at 25 °C (lit.)
Documentation: see Safety & Documentation for available documents
Featured Industry: Flavors and Fragrances
Organoleptic: banana; oily; fruity; whiskey
food allergen: no known allergens
SMILES string: CC(C)CCO
InChI: 1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3
InChI key: PHTQWCKDNZKARW-UHFFFAOYSA-N

Isoamyl alcohol (3-methylbutan-1-ol) that can be biologically produced is among the possible alcohols usable as an alternative fuel in internal combustion engines. 
Isoamyl alcohol has a higher energy density than smaller alcohols (ca. 28.5 MJ/L, as compared to ca. 21 MJ/L for ethanol and 27 MJ/L for 1-butanol). 
Isoamyl alcohol is less hydroscopic than ethanol and mixes better with hydrocarbons. 
To better understand the combustion characteristics of that alcohol, new experimental data were obtained for its kinetics of oxidation in a jet-stirred reactor (JSR). 

Concentration profiles of stable species were measured in a JSR at 10 atm over a range of equivalence ratios (0.35−4) and temperatures (530−1220 K). 
The oxidation of Isoamyl alcohol was modeled using an extended detailed chemical kinetic reaction mechanism (2170 reactions involving 419 species) derived from a previously proposed scheme for the oxidation of a variety of fuels. 
The proposed mechanism shows good agreement with the present experimental data. 
Reaction path and sensitivity analyses were conducted for interpreting the results.

Isoamyl alcohol reduced growth and induced filament formation in Saccharomyces cerevisiae. 
Isoamyl alcohol-induced filamentation was accompanied by an almost threefold greater increase in the specific activity of succinate dehydrogenase than in untreated cells, which suggested that isoamyl alcohol treatment caused the cells to produce more mitochondria than in normal yeast form proliferation. 
This was supported by measuring the dry weight of purified, isolated mitochondria. 
Filaments have an increased chitin content which is distributed over the majority of their surface, and is not confined to bud scars and the chitin ring between mother and daughter cells as in yeast-form cells.

Isoamyl alcohol
3-Methyl-1-butanol
Isopentyl alcohol
3-Methylbutan-1-ol
123-51-3
Isoamyl alcohol
3-Methylbutanol
1-Butanol, 3-methyl-
Isoamylol
Isobutylcarbinol
Iso-amylalkohol
Fusel Oil
Iso-amyl alcohol
2-Methyl-4-butanol
Isobutyl carbinol
ISOAMYLALCOHOL
Alcool isoamylique
Fermentation amyl alcohol
Alcool amilico
Amylowy alkohol
Isoamyl alkohol
i-Amyl Alcohol
Primary isoamyl alcohol
3-Metil-butanolo
isopentan-1-ol
MFCD00002934
Isoamyl alcohol (natural)
isoamyl-alcohol
3-Methyl-Butan-1-Ol
Isoamyl alcohol, primary
UNII-DEM9NIT1J4
3-methyl-Butanol
NSC 1029
Methyl-3-butan-1-ol
Butan-1-ol, 3-methyl
DEM9NIT1J4
Fuseloel
Huile de fusel
CHEBI:15837
3-METHYL-BUTAN-(1)-OL
3-Methyl-1-butanol, ACS reagent
iso-pentanol
WLN: Q2Y1 & 1
3-Methyl-1-butanol, 98%, pure
FEMA Number 2057
Isoamyl alkohol [Czech]
Alcool amilico [Italian]
Amylowy alkohol [Polish]
Iso-amylalkohol [German]
1-Hydroxy-3-Methylbutane
Alcool isoamylique [French]
3-Metil-butanolo [Italian]
FEMA No. 2057
HSDB 605
EINECS 204-633-5
Isopentyl alcohol (8CI)
3-Methyl-1-butanol, 99%, for biochemistry, AcroSeal(R)
iso-amylalcohol
isopentylalcohol
Isopentylalkohol
AI3-15288
CCRIS 8806
3-methylbutanoI
3-methyl butanol
3-methyl 1-butanol
3-methyl-1 butanol
3-methylbutane-1-ol
Butanol, 3-methyl-
Isoamyl alcohol (primary and secondary)
ACMC-1ADLL
6423-06-9
DSSTox_CID_5469
EC 204-633-5
DSSTox_RID_77799
DSSTox_GSID_25469
3-Methyl-1-butanol, 98%
CHEMBL372396
QSPL 002
DTXSID3025469
Isoamyl alcohol, >=98%, FG
NSC1029
NSC7905
3-Methyl-1-butanol, for analysis
ZINC896830
Isoamyl alcohol (3-methyl butanol)
NSC-1029
NSC-7905
1-$l^{1}-oxidanyl-3-methylbutane
3-Methylbutanol, analytical standard
EINECS 229-179-5
Tox21_302359
7340AF
ANW-18132
LMFA05000108
STL282718
3-Methyl-1-butanol A.C.S. Reagent
3-Methyl-1-butanol, LR, >=98%
AKOS000118739
Magnesium bis(3-methylbutan-1-olate)
NATURAL ISOAMYL ALCOHOL P & F
DB02296
MCULE-7411270401
3-Methyl-1-butanol, mixture of isomers
3-Methyl-1-butanol, p.a., 99.8%
Isoamyl alcohol, natural, >=98%, FG
3-Methyl-1-butanol, analytical standard
NCGC00255329-01
3-Methyl-1-butanol, anhydrous, >=99%
CAS-123-51-3
3-Methyl-1-butanol, reagent grade, 98%
3-Methyl-1-butanol, technical grade, 95%
ISOAMYL ALCOHOL ULTRA PURE GRADE 1L
FT-0616032
I0289
1973-EP2281899A2
1973-EP2316937A1
3-Methyl-1-butanol, ACS reagent, >=98.5%
3-Methyl-1-butanol, biotech. grade, >=99%
3-Methyl-1-butanol, ReagentPlus(R), >=99%
C07328
74374-EP2269986A1
74374-EP2308857A1
74374-EP2380568A1
NATURAL ISOAMYL ALCOHOL - TECHNICAL GRADE
117932-EP2287147A2
117932-EP2298768A1
3-Methyl-1-butanol, SAJ first grade, >=96.0%
Q223101
3-Methyl-1-butanol, JIS special grade, >=98.0%
F0001-0367
Z955123582
1-Butanol, 3-methyl-
1-Hydroxy-3-methylbutane
2-Methyl-4-butanol
3-Methyl-1-Butanol
3-Methyl-butan-(1)-ol
3-methyl-Butanol
3-Methylbutan-1-ol
3-methylbutanoI
3-Methylbutanol
3-Metil-butanolo
Alcool amilico
Alcool isoamylique
Amylowy alkohol
Butan-1-ol, 3-methyl
Butanol, 3-methyl-
Fermentation amyl alcohol
Fusel oil
Fuseloel
Huile de fusel
I-amyl alcohol
Iso-amyl alcohol
Iso-amylalkohol
Isoamyl alcohol
Isoamyl alkohol
Isoamylalcohol
isoamylol
Isobutyl carbinol
Isobutylcarbinol
Isopentan-1-ol
Isoamyl alcohol
Isopentyl alcohol
Isopentylalkohol
Methyl-3-butan-1-ol
primary isoamyl alcohol
Isopentyl alcohol, 1-(14)C-labeled
Isopentyl alcohol, barium salt
Isopentyl alcohol, lead (2+) salt
Isopentyl alcohol, magnesium salt
Isopentyl alcohol, potassium salt
Isopentyl alcohol, sodium salt
Isopentyl alcohol, strontium salt
Isoamyl alcohol (3-methyl butanol)
Isoamyl alcohol (natural)