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
Show more names
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
- Formal charge
- 0
- Complexity
- 25.1
Experimental & physicochemical properties
LogP
log Kow= 1.16
1.16
1.28
1.16
Odor
CHARACTERISTIC, DISAGREEABLE ODOR
Disagreeable odor.
Density
0.81 at 68 °F (USCG, 1999) - Less dense than water; will float
0.813 @ 15 °C/4 °C
Relative density (water = 1): 0.8
0.807 - 0.813
0.81 at 68 °F
0.8104 @ 20°C
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
- Hazard statements
- 226 · H226-H315-H318-H332-H335
- Precautionary statements
- 210 · P210-P233-P280-P303+P361+P353-P304+P340+P312-P305+P351+P338
Safety & regulation
GHS classification
GHS Classification
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
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.)
Fire Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Flammable. Above 42 °C explosive vapour/air mixtures may be formed.
FDA Requirements
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 & protection
Fire Fighting
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
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
Excerpt from NIOSH Pocket Guide for Isoamyl alcohol (primary):
(General first aid procedures)
Exposure Control and Personal Protection
4452.0 [ppm]
20.0 [ppm]
Fire Fighting Procedures
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.
Storage Conditions
IN GENERAL, MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, & SHOULD BE PERIODICALLY INSPECTED ... INCOMPATIBLE MATERIALS SHOULD BE ISOLATED FROM EACH OTHER.
Remove source of ignition. Keep containers closed. Store in prescribed, controllable places.
Cleanup Methods
1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quantities, absorb on paper towels. Evaporate in a safe place (such as a fume hood). Allow sufficient time for evaporating vapors to completely clear the hood ductwork. Burn the paper in a suitable location away from combustible materials. ... Isoamyl alcohol should not be allowed to enter a confined space, such as a sewer, because of the possibility of an explosion.
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Spray into the furnace. Incineration will become easier by mixing with a more flammable solvent.
1. By absorbing it in vermiculite, dry sand, earth or a similar material and disposing in a secured sanitary landfill. 2. By atomizing in a suitable combustion chamber.
Spillage Disposal
Personal protection: protective clothing, safety goggles and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable non-plastic containers as far as possible. Absorb liquid in sand or inert absorbent. Wash away remainder with plenty of water.
Preventive Measures
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
For more Preventive Measures (Complete) data for ISOAMYL ALCOHOL (7 total), please visit the HSDB record page.
Toxicology
Body Burden
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
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.
Environmental Fate
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
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).
Exposure Routes
The substance can be absorbed into the body by inhalation and by ingestion.
inhalation, ingestion, skin and/or eye contact
Signs and Symptoms
Sore throat. Cough. Burning sensation.
Dry skin. Redness.
Redness. Pain.
Abdominal pain. Headache. Drowsiness. Weakness. Nausea. Vomiting. Unconsciousness.
irritation eyes, skin, nose, throat; headache, dizziness; cough, dyspnea (breathing difficulty), nausea, vomiting, diarrhea; skin cracking; In Animals: narcosis
Effluent Concentrations
In an analysis of 455 wastewater samples from 35 industrial categories, isopentanol was only identified in 1 sample from the synfuels industry(2). In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, isopentanol was identified in discharges of the following industrial category (positive occurrences, median concn in ppb): synfuels (7; 39.8), publicly owned treatment works (1; 176.7). The highest effluent concn was in a publically-owned treatment works at 177 ppb(3). The mean and range of isopentanol emissions from four whiskey fermentation vats was 0.166 and 0.141-0.183 g per cu m of grain input, respectively(1). The maximum concn of isopentanol in the vat gas was about 9 mg/cu m and occurred 40 hr into the process(1).
Medical Surveillance
Employees should be screened for history of certain medical conditions which might place the employee at increased risk from isoamyl alcohol exposure. /These include/ skin disease ... liver disease ... kidney disease ... /and/ chronic respiratory disease. ... Any employee developing the above-listed conditions should be referred for further medical examination.
Soil Adsorption/Mobility
The Koc for isopentanol estimated from its water solubility, 26.7 mg/L(1), using recommended regression equations are 720(2) and 679(4). However, the chemicals used in developing these equations were mainly pesticides and their structures are not similar to isopentanol. The Koc for isopentanol estimated from molecular structure is 4(3). This should be a reasonable estimate for the Koc because it is close to the experimental value for the structurally similar chemical, 1-pentanol, 1.6(6). According to a suggested classification scheme(5), the estimated Kocs based on molecular structure suggests that isopentanol is very highly mobile in soil(SRC).
Natural Pollution Sources
Isopentanol is a plant volatile(2-6) and is also emitted from animal wastes(2,7) and by microorganisms(2). Isopentanol is the principal component of fusel oil, a by-product of alcoholic fermentation of starches and sugars(1).
CONSTITUTES MAJOR PORTION OF FUSEL OIL; ALSO KNOWN AS FERMENTATION AMYL ALCOHOL. ... IDENTIFIED AS ESTER AMONG CONSTITUENTS OF ROMAN CAMOMILE OIL, & IN SEVERAL ESSENTIAL OILS ... ALSO IN AROMAS OF STRAWBERRY & RASPBERRY; IDENTIFIED IN RUM.
Regulatory information
FDA Requirements
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
... 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
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
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. Production
2023: 50,000 - <75,000 lb
(1962) 5.5-6.8X10+9 GRAMS (ALL AMYL ALCOHOLS)
Methods of Manufacturing
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
MAJOR COMPONENT OF COMMERCIAL AMYL ALCOHOL, FUSEL OIL & POTATO-SPIRIT OIL.
GRADE: TECHNICAL
FUSEL OIL
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Cosmetics -> Solvent
General Manufacturing Information
Mining (except Oil and Gas) and support activities
1-Butanol, 3-methyl-: ACTIVE
Suppliers50 total
Additional notes
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
Linked notes
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