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89-82-7

Basic Information
CAS No.: 89-82-7
Name: (+)-PULEGONE
Article Data: 60
Molecular Structure:
Molecular Structure of 89-82-7 ((+)-PULEGONE)
Formula: C10H16 O
Molecular Weight: 152.236
Synonyms: Cyclohexanone,5-methyl-2-(1-methylethylidene)-, (R)-;p-Menth-4(8)-en-3-one, (R)-(+)- (8CI);(+)-(R)-Pulegone;(+)-Pulegone;(1R)-(+)-p-Menth-4(8)-en-3-one;(1R)-Pulegone;(R)-(+)-Pulegone;(R)-(+)-p-Menth-4(8)-en-3-one;(R)-Pulegone;NSC 15334;Pulegon;Pulegone;d-Pulegone;90449-51-7;
EINECS: 201-943-2
Density: 0.937g/mLat 25°C(lit.)
Melting Point: <=25°C
Boiling Point: 224°C(lit.)
Flash Point: 185°F
Appearance: clear colorless to yellow liquid
Hazard Symbols:
Risk Codes: 22
Safety: Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating vapors.
PSA: 17.07000
LogP: 2.71190
Synthetic route
Conditions
ConditionsYield
With sodium hydroxide In methanol; water100%
308358-04-5

(6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one

89-82-7

pulegone

Conditions
ConditionsYield
With molybdenum hexacarbonyl In benzene for 1h; Heating;93%
Conditions
ConditionsYield
With hydrogen; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; [Rh(cyclooctadiene)2](PF6); [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide In ethyl acetate at 50℃; under 22502.3 Torr; for 20h; Product distribution / selectivity;90%
copper-zinc-aluminum catalyst at 150℃; for 8h; Product distribution / selectivity;87%
BrPPh3(CH2)4PPh3Br

BrPPh3(CH2)4PPh3Br

491-09-8

3-terpinolenone

89-82-7

pulegone

Conditions
ConditionsYield
[Rh(cod)2]PF6 In ethyl acetate90%
23733-71-3

(R)-(+)-pulegone semicarbazone

89-82-7

pulegone

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 8h; Ambient temperature;64%
594-19-4

tert.-butyl lithium

66448-75-7, 125225-97-0, 125226-00-8

(5R)-2-(1-Chloro-1-methylethyl)-5-methylcyclohexanone

A

125137-92-0

(R)-2,2,5,9-Tetramethyldec-8-en-3-one

B

89-82-7

pulegone

Conditions
ConditionsYield
In tetrahydrofuran; pentane at -78℃; for 1h;A 63%
B 36%
491-09-8

3-terpinolenone

A

22472-80-6

syn-(-)-pulegol

B

89-82-7

pulegone

Conditions
ConditionsYield
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; bis(triphenylphosphane)copper(I) nitrate; hydrogen; sodium t-butanolate In isopropyl alcohol at 50℃; under 37503.8 Torr; for 18h; optical yield given as %ee; enantioselective reaction;A n/a
B 52%
594-19-4

tert.-butyl lithium

86613-13-0, 125225-99-2, 125353-54-0

(5R)-2-(1-Bromo-1-methylethyl)-5-methylcyclohexanone

A

125137-92-0

(R)-2,2,5,9-Tetramethyldec-8-en-3-one

B

89-82-7

pulegone

Conditions
ConditionsYield
In tetrahydrofuran; pentane at -78℃;A 31%
B n/a
18951-85-4

(R)-citronellic acid

108-24-7

acetic anhydride

89-82-7

pulegone

Conditions
ConditionsYield
With sulfuric acid Edukt 1 ist partiell racem.;
77732-35-5

(+)-citronelloyl chloride

89-82-7

pulegone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; potassium carbonate Yield given. Multistep reaction;
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Chemistry

Chemical Name: (+)-Pulegone
IUPAC NAME: 5-Methyl-2-propan-2-ylidenecyclohexan-1-one
CAS No.: 89-82-7
EINECS: 201-943-2
Molecular Formula: C10H16O
Molecular Weight: 152.23 g/mol
Density: 0.923 g/cm3 
Flash Point: 92.5 °C
Boiling Point: 224 °C at 760 mmHg
Storage temp.: 2-8°C
Following is the structure of d-Pulegone (89-82-7):


Product Categories about d-Pulegone (89-82-7) are Aromatic Ketones (substituted) ; Biochemistry ; Monocyclic Monoterpenes ; Terpenes
The chemical synonymous of d-Pulegone (89-82-7) are (R)-(+)-P-Menth-4(8)-EN-3-one ; (R)-P-Menth-4(8)-EN-3-one ; (R)-(+)-Pulegone ; (R)-Pulegone ; (R)-(+)-5-Methyl-2-isopropylidencyclohexanone ; (R)-2-Isopropylidene-5-methylcyclohexanone ; R-(+)-2-Isopropylidene-5-methylcyclohexanone ; Pulegon

Toxicity Data With Reference

1.    

ivn-dog LDLo:330 mg/kg

    COREAF    Comptes Rendus Hebdomadaires des Seances de lAcademie des Sciences. 236 (1953),633.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes:
Xn: Harmful
Risk Statements about d-Pulegone (89-82-7):
R22 Harmful if swallowed.
Safety Statements about d-Pulegone (89-82-7):
S23 Do not breathe vapour.
S24/25: Avoid contact with skin and eyes.
Attention:
1. Storage: Store in a cool, dry place. Keep container closed when not in use.
2. Handling: Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Wash thoroughly after handling. Remove contaminated clothing and wash before reuse.