Isoamyl Alcohol

HCID 31260CAS 123-51-3

Basic information

Standard SMILES
CC(C)CCO
InChIKey
PHTQWCKDNZKARW-UHFFFAOYSA-N
Molecular formula
C5H12O
Average molar mass
88.15 g/mol
Monoisotopic mass
88.088815

Overview

Isoamyl alcohol is a colorless liquid with a mild, choking alcohol odor. Less dense than water, soluble in water. Hence floats on water. Produces an irritating vapor. (USCG, 1999)

Names & identifiers

Preferred name
Isoamyl Alcohol
IUPAC
3-methylbutan-1-ol
English name
3-Methyl-1-butanol
Molecular formula
C5H12O
Molecular weight
88.15

Names & synonyms

Isoamyl alcohol3-Methyl-1-butanolIsopentyl alcohol123-51-33-Methylbutan-1-olIsopentanol3-Methylbutanol1-Butanol, 3-methyl-IsoamylolIsobutylcarbinol2-Methyl-4-butanolIsobutyl carbinol
Show more names
Iso-amylalkoholISOAMYLALCOHOLAlcool isoamyliqueAmylowy alkoholIsoamyl alkoholAlcool amilicoFermentation amyl alcohol3-Metil-butanolo

Database identifiers

CAS
123-51-3、50858-14-5、6423-06-9
PubChem CID
31260
DTXSID
DTXSID3025469
ChEMBL
CHEMBL372396
ChEBI
CHEBI:15837
UNII
DEM9NIT1J4
EC Number
204-633-5、229-179-5、907-533-6
Nikkaji
J2.011G

Properties

Computed structural properties

XLogP
1.2
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 2nd degree
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty alcohols [FA05]
SolventsSolvents -> Alcohols (<C12)
CosmeticsSolvent
SpringerMaterials PropertiesBoiling point

Physicochemical properties

Melting point
-117.2 °C · -117.2 °C
Boiling point
132.5 °C · 132.5 °C
Density
0.813 g/cm3 · 0.813 g/cm3(Temp: 15 °C)
pka
15.24 · 15.24±0.10(Predicted)
Symbol(GHS)
2 · GHS02,GHS05,GHS07
Signal word
Danger

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H226 (99.2%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2589 reports by companies from 47 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H226 (52.2%): Flammable liquid and vapor [Warning Flammable liquids]

Hazard information

Regulatory Information · 6 items

Chemical: 1-Butanol, 3-methyl-

Regulation (EC) No 1831/2003 (amended)

1-Butanol, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Butanol, 3-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13936

1-Butanol, 3-methyl-: HSNO Approval: HSR001172 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
DOT LabelFlammable Liquid
Fire Hazards · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Flammable. Above 42 °C explosive vapour/air mixtures may be formed.

Fire PotentialMODERATE, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT VIGOROUSLY WITH REDUCING MATERIALS.
Health HazardsVery high vapor concentrations irritate eyes and upper respiratory tract. Continued contact with skin may cause irritation. (USCG, 1999)

Safety & protection

Fire Fighting · 2 items

Fire Extinguishing Agents: Water spray, dry chemical, alcohol foam, or carbon dioxide. (USCG, 1999)

Use water spray, alcohol-resistant foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give nothing to drink. Do NOT induce vomiting. Refer immediately for medical attention.

First Aid · 2 items

Excerpt from NIOSH Pocket Guide for Isoamyl alcohol (primary):

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants and reducing agents.
Exposure Control and Personal Protection · 2 items

4452.0 [ppm]

20.0 [ppm]

Fire Fighting Procedures · 2 items

Use water, powder, "alcohol" foam or carbon tetrachloride. Water spray is effective for cooling fire-exposed containers, dispersing spills before burning, and protection from heat those persons engaged to stop leakage during the fire.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical.

Toxicology

Body Burden · 1 item

In a study in which the exhaled breaths of 26 smokers and 43 non-smokers were analyzed, 16% of the breaths of non-smokers and 77% of that of smokers contained isopentanol(1). In an earlier study of components of expired air of 8 male volunteers, three of the eight contained isopentanol and were expired at 2.6, 0.002, and 0.11 ug/hr(2). Two of these subjects were smokers(2). The isopentanol was believed to be of metabolic origin(2). As part of EPA's National Human Adipose Tissue Survey, 46 composite adipose fat samples were analyzed. Eighty-three percent of these samples contained isopentanol ranging from 1.51 to 14.82 ppm(3).

Interactions · 1 item

The purpose of this study was to investigate whether isopentanol, the most abundant hiqher chain alcohol in alcoholic beverages, contributes to induction of different forms of hepatic p450s associated with consumption of these beverages. Induction of p450 by isopentanol alone and in combination with ethanol in cultured chick and rat hepatocytes. The forms of induced p450 were identified both enzymaticaly and immunochemically. In cultured chick hepatocytes, both isopentanol and ethanol induced p450 2E, but combined treatment with these alcohols had no greater effect than treatment with ethanol alone. In cultured rat hepatocytes, isopentanol alone did not induce p450 2E or 2B1/2 and had no effect on the ethanol mediated induction of p450 2E. However, isopentanol combined with ethanol caused a synergistic induction of p450 2B1/2 in cultered rat hepatocytes and an additive to synergistic induction of p450 2H1/2 in cultered chick hepatocytes.

Target OrgansEyes, skin, respiratory system, central nervous system
Environmental Fate · 3 items

TERRESTRIAL FATE: In view of isopentanol's relatively high vapor pressure, 2.37 mm Hg at 25 °C(1), moderate Henry's Law constant, 1.41X10-5 atm-cu m/mol(2), and low adsorptivity to soil, isopentanol would be expected to volatilize from dry and moist soil(SRC). It is highly mobile in soil and should leach. Isopentanol is readily biodegraded in screening tests as well as in water grab sample tests and therefore would be expected to biodegrade in soil. (SRC)

AQUATIC FATE: If released in water, isopentanol will be lost by volatilization. The volatilization half-life of isopentanol from a model river estimated from its Henry's Law constant, 1.41X10-5 atm-cu m/mol(1), is 2.55 days(2). It should also biodegrade. The half-life of isopentanol in groundwater, river water and Lake Superior harbor water in Minnesota were 15, 11, and 6.1 days, respectively(3). Isopentanol would not be expected to adsorb to sediment or bioconcentrate in aquatic organisms.

ATMOSPHERIC FATE: Isopentanol will react with photochemically-produced hydroxyl radicals in the atmosphere. The rate constant estimated for this reaction is 7.8X10-12 cu cm/molec-sec(1). Assuming a hydroxyl radical concn of 5X10+5 radicals/cu cm, the half-life of isopentanol in the atmosphere will be 2.0 days(SRC).

Food Survey Values · 1 item

Isopentanol has been identified, but not quantified, in peanut oil(1), blue cheese(2) and a cheese made in the French Alps(3), filberts(4), beer(5), wine(7), meat(8-9), chickpeas(10), oranges(11), bananas(12), Concord grapes(13), and nectarines(6). Eighty proof whiskey contained 154.4 mg/L of isopentanol(14).

Adverse EffectsNeurotoxin - Acute solvent syndrome

Regulatory information

FDA Requirements · 1 item

Isoamyl alcohol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.

Safety data

Signal word
Danger
Symbol(GHS)
GHS02,GHS05,GHS07
Hazard statements
H226-H315-H318-H332-H335
Precautionary statements
P210-P233-P280-P303+P361+P353-P304+P340+P312-P305+P351+P338

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

... OXIDIZED BY WAY OF CORRESPONDING ALDEHYDES & FATTY ACIDS ... MAIN SITE OF PRIMARY OXIDATION APPEARS TO BE LIVER ... GLUCURONIC CONJUGATION TAKES PLACE TO EXTENT OF 9% ... ISOLATED IN URINE OF RABBITS.

... Small amounts of ... 3-methyl-1-butanol /are/ excreted in the air or urine following ip injections of 1 g/kg to rats: Percent excreted: 0.97 expired air; 0.27 urine; and 1.24 total. /From table/

Absorption, Distribution and Excretion · 1 item

3-Methyl-1-butanol, following serial (four 15-minute intervals) ip injections in the rat, is very rapidly metabolized ... . Only 1-1.5% of the administered doses of 3-methyl-1-butanol were excreted in the expired air plus urine as the pentanol. The blood concentration of 3-methyl-1-butanol decreased from 37 mg/100 ml at 1 hr (ie, 15 min after the last pentanol injection) to <1 mg/100 ml at 5 hr. In the rabbit, limited amounts of 3-methyl-1-butanol and the other primary pentanols are conjugated to yield the glucuronide, and 7-10% of the administered dose is excreted as the urinary glucuronide.

Uses & manufacturing

Uses · 5 items

Used as a solvent, paint stripper, and intermediate in the photographic and pharmaceutical industries; [ACGIH]

Painting (Solvents) [Category: Paint]

SYNTHETIC FLAVOR; INTERMEDIATE IN PREPN OF PHARMACEUTICALS; FOR ISOAMYL ACETATE AND OTHER ESTERS; FOR DITHIOPHOSPHATE ESTERS (LUBRICATING OIL ADDITIVE AND HYDRAULIC FLUID ADDITIVE)

SOLVENT FOR FATS, RESINS, ALKALOIDS, ETC; MFR ISOAMYL (AMYL) COMPD, ISOVALERIC ACID, MERCURY FULMINATE; MFR PYROXYLIN, ARTIFICIAL SILK, LACQUERS, SMOKELESS POWDERS; IN MICROSCOPY; FOR DEHYDRATING CELLOIDIN SOLN; FOR DETERMINING FAT IN MILK

REPORTED USES: NON-ALCOHOLIC BEVERAGES 17 PPM, ALCOHOLIC BEVERAGES 100 PPM, ICE CREAM, ICES, ETC 7.6 PPM, CANDY 52 PPM, BAKED GOODS 24 PPM, GELATINS & PUDDINGS 46 PPM, CHEWING GUM 300 PPM.

U.S. Imports(1984) 1.89X10+8 G /AMYL ALCOHOLS/
U.S. Production · 2 items

2023: 50,000 - <75,000 lb

(1962) 5.5-6.8X10+9 GRAMS (ALL AMYL ALCOHOLS)

Industry UsesSolvent
Methods of Manufacturing · 4 items

FROM ISOBUTYLENE, VIA THE OXO PROCESS

FROM LIGHT PETROLEUM BY FRACTIONAL DISTILLATION, DEHYDRATION OF PENTANE FRACTION WHICH IS THEN HEATED & RE-FRACTIONATED, & AMYLCHLORIDE FRACTION AGAIN FRACTIONALLY DISTILLED, GIVING MONO-CHLORO-PENTANE MIXTURE. THIS IS SUBJECTED TO HYDROLYSIS WITH SODIUM OLEATE SOLN IN PRESENCE OF CATALYST.

... MFR BY FRACTIONATION OF FUSEL OIL & VIA CHLORINATION OF PENTANES, & PROPERTIES

PREPN FROM BUTADIENE, CARBON MONOXIDE, WATER, PLUS CATALYST; FROM METHYLBUTENES

Formulations/Preparations · 3 items

MAJOR COMPONENT OF COMMERCIAL AMYL ALCOHOL, FUSEL OIL & POTATO-SPIRIT OIL.

GRADE: TECHNICAL

FUSEL OIL

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Isoamylol is an primary alcohol that is butan-1-ol in which a hydrogen at position 3 has been replaced by a methyl group. It has a role as a xenobiotic metabolite, a Saccharomyces cerevisiae metabolite and an antifungal agent. It is a primary alcohol, a volatile organic compound and an alkyl alcohol. It derives from a hydride of an isopentane.

Related reactions

417 records

Linked notes

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