2-Heptanone

HCID 8051CAS 110-43-0

Grundinformationen

Standard-SMILES
CCCCCC(C)=O
InChIKey
CATSNJVOTSVZJV-UHFFFAOYSA-N
Summenformel
C7H14O
Durchschnittliche Molmasse
114,19 g/mol
Monoisotopische Masse
114,10446507

Überblick

N-amyl methyl ketone appears as a clear colorless liquid. Flash point 126 °F. Less dense than water and only slightly soluble in water. Hence floats on water. Vapors heavier than air. Density 6.8 lb / gal. Used as a synthetic flavoring and in perfumes.

Namen und Bezeichner

Bevorzugter Name
2-Heptanone
IUPAC
heptan-2-one
Lokaler Name
2-Heptanon
Englischer Name
2-Heptanone
Summenformel
C7H14O
Molmasse
114.19

Namen und Synonyme

2-HEPTANONEHeptan-2-one110-43-0Methyl pentyl ketoneButylacetoneAmyl methyl ketoneMethyl amyl ketoneMethyl n-amyl ketonen-Amyl methyl ketonen-Pentyl methyl ketonePentyl methyl ketoneMethyl n-pentyl ketone
Weitere Namen anzeigen
MAKHeptanone2-Heptanon2-HeptanalHeptan-2-on2-Ketoheptane2-Heptanone, pure, 98%
Ketone, methyl pentylAmyl-methyl-cetoneMethyl-amyl-cetoneKetone C-7Methyl-n-amylketoneFEMA No. 2544FEMA Number 2544DTXSID5021916

Datenbank-Bezeichner

CAS
110-43-0
PubChem CID
8051
DTXSID
DTXSID5021916
ChEMBL
CHEMBL18893
ChEBI
CHEBI:5672
UNII
89VVP1B008
EC Number
203-767-1
Nikkaji
J5.091A

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
4
Schwere Atome
8

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 2nd degree
LipidsFatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SolventsSolvents -> Ketones (<C12)
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (2-Heptanone) -> IFRA transparency List
LogP · 3 Einträge

log Kow = 1.98

1.98

2.08

Physikochemische Eigenschaften

Schmelzpunkt
-35 °C · -35 °C (lit.)
Siedepunkt
149 · 149-150 °C (lit.)
Dichte
0.82 g/mL · 0.82 g/mL at 25 °C (lit.)
Dampfdichte
3.94 · 3.94 (vs air)
Dampfdruck
2.14 mm · 2.14 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.408(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 3241) of reports.

Warning

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: 2-Heptanone

Regulation (EC) No 1831/2003 (amended)

2-Heptanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Heptanone 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: 06-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/10230

2-Heptanone: HSNO Approval: HSR001084 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 InformationIMAP assessments - 2-Heptanone: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 4 Einträge

Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire.

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Above 48 °C explosive vapour/air mixtures may be formed.

Fire PotentialA flammable liquid when exposed to heat or flame ...
Health Hazards · 3 Einträge

Inhalation can cause headache, fatigue, nausea, vomiting, dizziness, stupor, drowsiness, disturbed vision, and unconsciousness. Skin contact can cause moderate irritation, defatting, and dermatitis. Ingestion may cause irritation of lips and mouth, gastro-intestinal irritation, nausea, diarrhea, drowsiness, loss of consciousness, weak and rapid pulse, cold-pale complexion. (USCG, 1999)

· Inhalation or contact with material may irritate or burn skin and eyes.

· Inhalation or contact with material may irritate or burn skin and eyes.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

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

First Aid Measures · 4 Einträge

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.

Accidental Release Measures · 4 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 4 Einträge

Excerpt from NIOSH Pocket Guide for Methyl (n-amyl) ketone:

General First Aid:

General First Aid:

(General first aid procedures)

Safe StorageFireproof.
Exposure Control and Personal Protection · 2 Einträge

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxikologische Informationen

Body Burden2-Heptanone was found in 36 of 46 samples analyzed for the National Human Adipose Tissue Survey, FY 1982(1).
Interactions · 3 Einträge

Chloroform-induced liver injury was evaluated in male rats pretreated (15 mmol/kg, orally) with 2-heptanone. After 18 hr, a challenging dose of chloroform (0.50 or 0.75 ml/kg ip) was given. Liver damage was evaluated 24 hr after chloroform admin by determining elevations in plasma glutamic-pyruvic transaminase and ornithine carbamyl transferase activity. 2-Heptanone potentiated chloroform-induced liver damage.

When methyl n-amyl ketone (456 mg/kg) was administered with equimolar doses of MnBK (methyl n-butyl ketone) by subcutaneous injection 5 days/week for 20 week, the neurotoxicity of MnBK, as measured by motor fiber conduction velocity and motor distal latency, was enhanced (p<0.01) ...

Chloroform (CHCl3)-induced hepato- and nephrotoxicity was evaluated in male, Fischer 344 rats pretreated with various dosages (1.0 to 15.0 mmol/kg, /orally/) of acetone (Ac), 2-butanone (Bu), 2-pentanone (Pn), 2-hexanone (Hx), or 2-heptanone (Hp). The CHCl3 challenge dosage (0.5 ml/kg, ip) produced slight centrilobular hydropic degeneration and patchy degeneration and necrosis in the proximal tubules of corn oil-pretreated rats. Each of the ketones studied produced a dose-related potentiation of CHCl3 liver and kidney injury. CHCl3 produced extensive tubular and centrilobular necrosis when administered to ketone-pretreated rats. The relationship between ketone dosage and the magnitude of the potentiated response was nonlinear. Maximum potentiation of CHCl3 toxicity occurred in the dosage range of 5.0 to 10.0 mmol ketone/kg. Ketone dosages greater than 10.0 mmol/kg were associated with a reduction in the degree of CHCl3 injury. At the lowest ketone dosage (1.0 mmol/kg), potentiating capacity appeared to be related to ketone carbon skeleton length. No differences in potentiating capacity were discernable between the ketones at dosages of 5.0 to 10.0 mmol/kg.

Target OrgansEyes, skin, respiratory system, central nervous system, peripheral nervous system
Ecotoxicity Values · 1 Eintrag

LC50 Pimephales promelas (Fathead minnow) 131 mg/L/96 hr (confidence limit 126-137 mg/L), flow-through bioassay with measured concentrations, 24.2 °C, dissolved oxygen 7.2 mg/L, hardness 46.4 mg/L calcium carbonate, alkalinity 42.1 mg/L calcium carbonate, and pH 7.72.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 280(SRC), determined from a log Kow of 1.98(2) and a regression-derived equation(3), indicates that 2-heptanone is expected to have moderate mobility in soil(SRC). Volatilization of 2-heptanone from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.69X10-4 atm-cu m/mole(4). 2-Heptanone is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.85 mm Hg(5). Screening studies indicate that 2-heptanone is likely to biodegrade in aquatic systems under aerobic conditions(6-9).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 280(SRC), determined from a log Kow of 1.98(2) and a regression-derived equation(3), indicates that 2-heptanone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.69X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.8 hours and 6 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 7(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Screening studies indicate that 2-heptanone is likely to biodegrade in aquatic systems under aerobic conditions(7-10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-heptanone, which has a vapor pressure of 3.85 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-heptanone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.4 days(SRC), calculated from its rate constant of 1.17X10-11 cu cm/molecule-sec at 25 °C(3). Although 2-heptanone has the potential of being removed from the atmosphere by direct photochemical degradation(4), the rate of this process is not expected to be able to compete with atmospheric removal by the reaction with hydroxyl radicals(SRC).

Food Survey Values · 1 Eintrag

2-Heptanone was detected as a volatile flavor component of roasted filberts(1), baked potatoes(2), blue cheese(3), Beaufort (Gruyere) cheese(4), fried bacon(5), clove essential oil(6), chickpeas(7), fried chicken(8), earth almonds (Cyperus esculentus L.)(14), frankfurters(15), raw beef(17), and in food products processed from the Cassava root(9). 2-Heptanone has been identified in swiss cheese (0.45 ppm) evaporated milk, butter, milk, cream (0.004-0.007 ppm), milk fat (16 ppm), white bread, soybeans (1 ppm) peaches and orange juice(10). 2-Heptanone has been measured in canned cream corn (6 ppb), canned corn (21 ppb), frozen corn (3 ppb) and fresh corn (18 ppb)(11). 2-Heptanone was found in popcorn using wet extraction method at 60 ug/kg and dry extraction method at 17 ug/kg(12). Commercial rice cakes were found to contain 15 ppb of 2-heptanone(13). Fermented soybean (Glycine max) curds were found to contain 601.7 to 972.6 ug/kg of 2-heptanone(16). 2-Heptanone was found in uncured beef (0.21 mg/kg), chicken (0.54 mg/kg) and pork (0.20 mg/kg)(18). 2-Heptanone was detected in whole and ground musty sorghum with direct helium-purge method and with supercritical fluid extraction method(19). 2-Heptanone was isolated as a volatile component of duck meat (5.68 ppb), duck fat (11.62 ppb), Cantonese style roasted duck (38.44 ppb) and Cantonese style roasted duck gravy (63.45 ppb)(20). 2-Heptanone was measured at 146 ng/g, 455 ng/g, 115 ng/g and 42 ng/g in anchovy paste, big eyed herring paste, hair tail viscera paste and shrimp paste, respectively(21).

Regulatorische Informationen

FDA Requirements · 1 Eintrag

2-Heptanone is a food additive permitted for direct addition to food for human consumption, as long as 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. Synthetic flavoring substances and adjuvants /incl 2-Heptanone/ may be safely used in foods.

FIFRA Requirements · 2 Einträge

Residues of 2-heptanone are exempted from the requirement of a tolerance when used as a solvent, co-solvent in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.

Residues of 2-heptanone are exempted from the requirement of a tolerance when used as a solvent, co-solvent in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.

Sicherheitsdaten

OEB
A
OEL
TWA: 100 ppm (465 mg/m3)
wgk
2
IDLA
800 ppm
tsca
TSCA listed
ridadr
UN 1110

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 4 Einträge

MnAK undergoes carbonyl reduction to a secondary alcohol and omega-1 oxidation to a hydroxyketone, which is further oxidized to 2,6-heptanedione.

When 950 mg methyl amyl ketone/kg body weight was administered orally to rabbits, 40% was excreted as heptyl-2-glucuronide, and traces of the unchanged ketone were also found in the urine. 2-Heptanone ... was identified ... among ... 300 compounds present in the volatile constituents of urine from male and female subjects.

A subchronic inhalation study was conducted in which male rats and monkeys were exposed to 0, 131, or 1025 ppm methyl n-amyl ketone for 10 mo (6 hr/day, 5 days/wk). Methyl n-amyl ketone and methyl n-amyl alcohol were detected in the urine and serum of monkeys exposed to methyl n-amyl ketone.

/It was/ reported that 41% of an orally administered dose of 0.95g/kg /methyl n-amyl ketone/ in rabbits was excreted as 2-heptyl glucuronide ...Inhibition of P450 2EL increases the amount of MnAK exhaled.

Absorption, Distribution and Excretion · 2 Einträge

Results of tissue distribution studies of (14)C methyl n-amyl ketone in rats comparing ip and inhalation routes of exposure were similar. Liver tissue had the highest level of radioactivity regardless of the route of admin; however, no liver pathology was observed. Urinary excretion accounted for 25% of the admin dose after 12 hr.

/It was/ reported that 41% of an orally administered dose of 0.95g/kg /methyl n-amyl ketone/ in rabbits was excreted as 2-heptyl glucuronide ...Inhibition of P450 2EL increases the amount of MnAK exhaled.

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 6 Einträge

Used as a solvent for resins and lacquers, a fragrance for cosmetics, and a flavor for foods; [HSDB]

Painting (Solvents) [Category: Paint]

Industrial solvent; solvent for synthetic resin finishes; fragrance ingredient in creams, lotions, perfumes, soaps & detergents; flavor ingredient in foods; inert reaction medium

Solvent for nitrocellulose lacquers.

Blue cheese flavor

In perfumery as constituent of artificial carnation oils; as industrial solvent

U.S. Production · 6 Einträge

2023: 100,000,000 - <250,000,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1972) GREATER THAN 4.54X10+5 G

(1975) GREATER THAN 4.54X10+5 G

(1986) >10 million-50 million pounds

For more U.S. Production (Complete) data for 2-HEPTANONE (8 total), please visit the HSDB record page.

Consumer UsesSolvent
Industry UsesSolvent
Methods of Manufacturing · 2 Einträge

Produced industrially by reductive condensation of acetone with butyraldehyde in one or two steps.

Prepd by the ketone decomposition of ethyl butylacetoacetate; by hydration of 1-heptyne and 2-heptyne

Formulations/PreparationsGRADE: Technical
Anwendungen · 3 Einträge

Beschreibung2-Heptanone has a characteristic banana, slightly spicy odor. It may be prepared by oxidation of methyl n-amyl carbinol; also from n-amyl propionic acid or from ethyl butyl acetat.

OccurrenceReported found in clove essential oil, Ceylon cinnamon and rancid coconut oil; also identifed in Ruta Montana Also reported found in banana, lingonberry, loganberry, black currant, guava, grapes, papaya, peach, pear, raspberry, other berries, strawberry jam, asparagus, roasted onion, leek, baked potato, mushroom, clove bud, ginger, blue, cheddar and Swiss cheeses, milk, cream, butter, fsh, meats, hop oil, beer, brandy, rum, malt whiskey, grape wines, cocoa, coffee, tea, peanuts, pecans, walnut, oats, soybeans, coconut oil, olive, passion fruit, mango, fgs, rice, sweet corn, corn tortillas, malt, caviar, shrimp, oysters, crab, crayfsh and mate

Verwenden2-Heptanone is used as an industrial solvent; a solvent for synthetic resin finishes; an inert reaction medium; a flavor ingredient in foods; a fragrance ingredient in creams, lotions, perfumes, soaps, and detergents.

Darstellung

synthetischeBy oxidation of methyl n-amyl carbinol; also from n-amyl propionic acid or from ethyl butyl acetate.

Anbieter50 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: Heptan-2-one is a dialkyl ketone with methyl and pentyl as the alkyl groups. It has a role as a pheromone and a mouse metabolite. It is a dialkyl ketone and a methyl ketone.

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