Product Name

  • Name

    (+)-PULEGONE

  • EINECS 201-943-2
  • CAS No. 89-82-7
  • Article Data60
  • CAS DataBase
  • Density 0.937g/mLat 25°C(lit.)
  • Solubility
  • Melting Point <=25°C
  • Formula C10H16 O
  • Boiling Point 224°C(lit.)
  • Molecular Weight 152.236
  • Flash Point 185°F
  • Transport Information
  • Appearance clear colorless to yellow liquid
  • Safety Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating vapors.
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 89-82-7 ((+)-PULEGONE)
  • Hazard Symbols
  • 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;
  • PSA 17.07000
  • LogP 2.71190

Synthetic route

Conditions
ConditionsYield
With sodium hydroxide In methanol; water100%
(6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one
308358-04-5

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

pulegone
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

3-terpinolenone
491-09-8

3-terpinolenone

pulegone
89-82-7

pulegone

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

(R)-(+)-pulegone semicarbazone

pulegone
89-82-7

pulegone

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

tert.-butyl lithium

(5R)-2-(1-Chloro-1-methylethyl)-5-methylcyclohexanone
66448-75-7, 125225-97-0, 125226-00-8

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

A

(R)-2,2,5,9-Tetramethyldec-8-en-3-one
125137-92-0

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

B

pulegone
89-82-7

pulegone

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

3-terpinolenone

A

syn-(-)-pulegol
22472-80-6

syn-(-)-pulegol

B

pulegone
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%
tert.-butyl lithium
594-19-4

tert.-butyl lithium

(5R)-2-(1-Bromo-1-methylethyl)-5-methylcyclohexanone
86613-13-0, 125225-99-2, 125353-54-0

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

A

(R)-2,2,5,9-Tetramethyldec-8-en-3-one
125137-92-0

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

B

pulegone
89-82-7

pulegone

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

(R)-citronellic acid

acetic anhydride
108-24-7

acetic anhydride

pulegone
89-82-7

pulegone

Conditions
ConditionsYield
With sulfuric acid Edukt 1 ist partiell racem.;
(+)-citronelloyl chloride
77732-35-5

(+)-citronelloyl chloride

pulegone
89-82-7

pulegone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; potassium carbonate Yield given. Multistep reaction;
(R)-citronellic acid
18951-85-4

(R)-citronellic acid

sulfuric acid
7664-93-9

sulfuric acid

acetic anhydride
108-24-7

acetic anhydride

pulegone
89-82-7

pulegone

(R)-citronellic acid-chloride

(R)-citronellic acid-chloride

pulegone
89-82-7

pulegone

Conditions
ConditionsYield
With carbon disulfide; tin(IV) chloride anschl. mit methanol. KOH;
Conditions
ConditionsYield
under 752 Torr; Erhitzen auf Siedetemperatur;

d-Pulegone Chemical Properties

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

d-Pulegone Toxicity Data With Reference

1.    

ivn-dog LDLo:330 mg/kg

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

d-Pulegone Consensus Reports

Reported in EPA TSCA Inventory.

d-Pulegone 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. 

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