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Allylisovalerat

Allyl isovalerate

HCID 17816
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Grundinformationen

CAS
2835-39-4
Standard-SMILES
C=CCOC(=O)CC(C)C
InChIKey
HOMAGVUCNZNWBC-UHFFFAOYSA-N
Summenformel
C8H14O2
Durchschnittliche Molmasse
142,2 g/mol
Monoisotopische Masse
142,09937969

Überblick

Allyl isovalerate is a clear colorless to pale yellow liquid with overripe fruit odor and an apple taste. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Allyl isovalerate
IUPAC
prop-2-enyl 3-methylbutanoate
Lokaler Name
Allylisovalerat
Englischer Name
ALLYL ISOVALERATE
Summenformel
C8H14O2
Molmasse
142.2

Namen und Synonyme

ALLYL ISOVALERATE2835-39-4Allyl isopentanoateAllyl isovalerianateIsovaleric acid, allyl ester2-Propenyl 3-methylbutanoate2-Propenyl isovalerateAllyl 3-methylbutyrateButanoic acid, 3-methyl-, 2-propenyl ester2-Propenyl isopentanoateprop-2-en-1-yl 3-methylbutanoateFEMA No. 2045
Weitere Namen anzeigen
FEMA 2045femano.20452-propenylisovalerateALLYL-3-METHYL BUTYRATE
3-Methylbutyric acid, allyl esterNCI-C54717Butyric acid, 3-methyl-, allyl ester3-Methylbutanoic acid, 2-propenyl esterDTXSID4039233Butanoic acid, 3-methyl-, 2-propen-1-yl esterNSC-186063551Z86V7T

Datenbank-Bezeichner

CAS
2835-39-4
PubChem CID
17816
DTXSID
DTXSID4039233
ChEMBL
CHEMBL1887355
ChEBI
CHEBI:82380

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
5
Schwere Atome
10
Formalladung
0
Komplexität
116

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Esters, Other
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]
OdorPLEASANT OVER-RIPE FRUIT ODOR
TasteAPPLE TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 Einträge

0.882 at 75 °F (NTP, 1992) - Less dense than water; will float

0.879-0.884

Flavoring AgentsEU Flavoring substances
Color/FormLIQUID
Solubility · 3 Einträge

less than 0.1 mg/mL at 61.7 °F (NTP, 1992)

Insoluble in water and miscible with perfume and flavour materials

1ml in 1ml 95% ethanol (in ethanol)

Flash Point · 2 Einträge

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P262, P264, P270, P280, P301+P316, P302+P352, P303+P361+P353, P316, P321, P330, P361+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1598 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Butanoic acid, 3-methyl-, 2-propenyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Butanoic acid, 3-methyl-, 2-propenyl ester: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Aliphatic allyl esters: Human health tier II assessment
DOT LabelFlammable Liquid Poison
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this chemical include skin irritation.
Hazards Summary · 1 Eintrag

A mutagen, tumorigen, and moderate skin irritant; Causes somnolence in lethal-dose feeding studies of rats; [RTECS] Emergency treatment: Irritants; [HSDB] Safe when used as a flavoring agent in food; ADI = 0-0.12 mg/kg bw; [JECFA] A skin irritant; [CAMEO]

FDA Requirements · 2 Einträge

172.515

121.1164

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Allyl isovalerate is metabolized to isovaleric acid, which can conjugate with glycine, and allyl alcohol, which could then be further metabolized via two pathways to form either acrolein or glycidol, from which a variety of metabolites could result (L1276).

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 3 Einträge

Used as a fragrance in creams and lotions and as a flavoring agent; [HSDB]

FRAGRANCE, EG, IN CREAMS & LOTIONS; FLAVORING AGENT IN FOODS, EG, BAKED GOODS

Allyl isovalerate has been used since the 1950s as a raw material for fragrances in cosmetics, lotions and perfumes and in certain food products, although it is not known whether it is currently used in this way (L1276).

U.S. Exports · 2 Einträge

(1977) No Data

(1979) No Data

U.S. Imports · 2 Einträge

(1977) No Data

(1979) No Data

U.S. Production · 2 Einträge

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 2 Einträge

DIRECT ESTERIFICATION OF ALLYL ALCOHOL WITH ISOVALERIC ACID UNDER AZEOTROPIC CONDITIONS

SYNTH BY DIRECT ESTERIFICATION IN PRESENCE OF BENZENE.

Use Classification · 3 Einträge

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Zugehörige Reaktionen

0
Reaktionsaufzeichnung erstellen

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
UNII
3551Z86V7T
EC Number
220-609-7
Nikkaji
J36.953E

103.5 °F (NTP, 1992)

40 °C

Boiling Point · 4 Einträge

306.1 °F at 729 mmHg (NTP, 1992)

89-90 °C

161.00 °C. @ 760.00 mm Hg

155 °C

Vapor Pressure · 2 Einträge

13 mmHg at 71.6 °F ; 16.8 mmHg at 86.0 °F (NTP, 1992)

13.0 [mmHg]

Physikochemische Eigenschaften

Siedepunkt
155 °C · 155 °C(lit.)
Dichte
0.88 g/mL · 0.88 g/mL at 25 °C(lit.)
FEMA
2045 · 2045 | ALLYL ISOVALERATE
Brechungsindex
20 · n20/D 1.416(lit.)
Flammpunkt
139 °F · 139 °F
Löslichkeit
Insoluble in water, soluble in alcohol, miscible with perfume and flavor materials. Poorly soluble in Propylene glycol.
Geruch (Odor)
Powerful winey-fruity, “fermented”, Applelike odor.
Biologische Quelle
synthetic
Geruchsart
fruity
JECFA Number
7 · 7
Major Application
flavors and fragrances
Kosmetik-Inhaltsstoffe Funktionen
PERFUMING
InChI
1S/C8H14O2/c1-4-5-10-8(9)6-7(2)3/h4,7H,1,5-6H2,2-3H3
InChIKey
HOMAGVUCNZNWBC-UHFFFAOYSA-N
SMILES
CC(C)CC(=O)OCC=C
LogP
2.4 · 2.40
EPA chemische Informationen
Allyl isovalerate (2835-39-4)
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special Reports · 2 Einträge

A REVIEW WITH 8 REF ON ALLYL ISOVALERATE INCLUDING TOXICITY, IRRITATION, SENSITIZATION, & METABOLISM.[OPDYKE DL J; FOOD COSMET TOXICOL 17 (SUPPL) 703 (1979)]

DHHS/NTP; Carcinogenesis Studies of Allyl Isovalerate in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 253 (1983) NIH Publication No.83-2509

Reactivity ProfileALLYL ISOVALERATE may react vigorously with strong oxidizing agents. Can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen. May react exothermically with both acids and bases.
Air and Water ReactionsInsoluble in water.
Hazard Classes and Categories · 2 Einträge

Flam. Liq. 3 (100%)

Acute toxicity (ingestion) - category 3

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

Toxikologische Informationen

Treatment · 1 Eintrag

Consider dilution with water or milk in case of ingestion. After inhalation, move patient to fresh air and monitor for respiratory distress. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. (T36)

Health EffectsHarmful in contact with skin and if swallowed. Exposure via inhalation may result in bronchospasm and rarely, upper airway swelling or acute lung injury (T36, L1275).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity Summary · 1 Eintrag

Allyl isovalerate has low irritancy potential. It is deduced that one of its metabolites, isovaleric acid, is toxic, based upon the effects of an inborn error of leucine metabolism caused by isovaleryl-coenzyme A dehydrogenase deficiency (L1276).

Signs and SymptomsIrritating to eyes, respiratory system, and skin. Headache, rhinorrhea, cough, shortness of breath, chest pain (L1275).
Ongoing Test Status · 1 Eintrag

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=2835-39-4]

Natural Pollution SourcesNOT REPORTED FOUND IN NATURE.
Carcinogen Classification · 6 Einträge

Allyl isovalerate

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 36: (1985) Allyl Compounds, Aldehydes, Epoxides and Peroxides

1999

1998

Allyl isovalerate

Non-Human Toxicity Excerpts · 1 Eintrag

Allyl isovalerate (AI) was evaluated for the induction of sex-linked recessive lethal mutations in Drosophila melanogaster by the National Toxicology Program. Canton-S wild-type males were treated with concentrations of AI that result in approximately 30% mortality. Following treatment, males were mated individually to 3 harems of Basc virgin females to produce 3 broods for analysis. All dietary concentrations (1200, 1600, 2000, and 4500 ppm) of AI tested gave negative results.

Evidence for Carcinogenicity · 1 Eintrag

Evaluation: No epidemiological data relevant to the carcinogenicity of allyl isovalerate were available. There is limited evidence in experimental animals for the carcinogenicity of allyl isovalerate. Overall evaluation: Allyl isovalerate is not classifiable as to its carcinogenicity to humans (Group 3).

National Toxicology Program Studies · 1 Eintrag

Carcinogenesis studies of allyl isovalerate (96% pure) were conducted by administering the test chemical in corn oil by gavage to groups of 50 male and 50 female F344/N rats and to groups of 50 male and 50 female B6C3F1 mice at doses of 31 or 62 mg/kg. ... Doses were admin five times per wk for 103 wk. Groups of 50 rats and 50 mice of each sex received corn oil by gavage on the same dosing schedule and served as vehicle controls. ... Under the conditions of these studies, allyl isovalerate ... /caused/ mononuclear cell leukemia in male F344/N rats and lymphoma in female B6C3F1 mice.

Toxicity DataLD50: 230 mg/kg (Oral, Rat) (L1275) LD50: 500 mg/kg (Oral, Mouse) (L1275) LD50: 560 mg/kg (Dermal, Rabbit) (L1275)

Regulatorische Informationen

FDA Requirements · 2 Einträge

172.515

121.1164

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 1992 3/PG 3
RTECS-Nr.
NY1412000
risk_code
21/22-36/37/38
Toxizität
mouse,LDLo,oral,500mg/kg (500mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)SKIN AND APPENDAGES (SKIN): HAIR: OTHER,National Toxicology Program Technical Report Series.
hazard_code
Xn
safety_code
26-36
hazard_class
3.2
packing_group
III
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
2835-39-4(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 OralEye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
General Manufacturing Information · 4 Einträge

Butanoic acid, 3-methyl-, 2-propen-1-yl ester: ACTIVE

REPORTED USES: NON-ALCOHOLIC BEVERAGES 8.6 PPM; ICE CREAM, ICES, ETC 18 PPM; CANDY 22 PPM; BAKED GOODS 15-48 PPM; GELATINS & PUDDINGS 1.0 PPM.

FLAVOR USEFUL IN: APPLE, CHERRY FRUIT BLENDS

FEMA NUMBER 2045

Anwendungen · 1 Eintrag

VerwendenAllyl Isovalerate is a synthetic flavoring agent that is a stable, color- less to light yellow liquid of fruity odor. it should be stored in glass or tin containers. it has usage in fruit flavors with applications in beverages, baked goods, ice cream, and candy at 8–50 ppm.

Darstellung

synthetischeBy direct esterification in the presence of benzene.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Concentrated sulfuric acidAllylalkoholl

Anbieter24 Anbieter

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