cis-Isolimonenol

cis-Isolimonenol - Names and Identifiers

Name	2-Cyclohexen-1-ol,1-methyl-4-(1-methylethenyl)-, (1S,4R)-
Synonyms	cis-Isolimonenol p-Mentha-2,8-dien-1-b-ol (+)-p-Mentha-2,8-dien-1-ol (1S,4R)-p-Menth-2,8-dien-1-ol (+)-cis-p-Mentha-2,8-dien-1-ol (+)-(1S,4R)-p-Mentha-2,8-dien-1-ol p-Mentha-2,8-dien-1-ol, stereoisomer(8CI) (1S,4R)-1-Methyl-4-(Prop-1-En-2-Yl)Cyclohex-2-Enol 2-Cyclohexen-1-ol,1-methyl-4-(1-methylethenyl)-, (1S,4R)- 2-Cyclohexen-1-ol,1-methyl-4-(1-methylethenyl)-, (1S-cis)-
CAS	22972-51-6

cis-Isolimonenol - Physico-chemical Properties

Molecular Formula	C10H16O
Molar Mass	152.23
Density	0.9398
Boling Point	69-70 °C(Press: 3 Torr)
Appearance	White solid
Storage Condition	2-8℃
Physical and Chemical Properties	Bioactive cis-Isolimonenol ((1S,4R)-p-Mentha-2,8-dien-1-ol) is a chemical component of essential oil.
Use	Application (1S,4R)-1-methyl -4-(1-methylvinyl)-2-cyclohexen-1-ol also known as trans-menthyl -2,8-diene -1-alcohol, can be used for the synthesis of cannabidiol (CBD). Cannabidiol is the main chemical component of the medicinal plant cannabis, extracted from female cannabis plants, is a non-addictive component of cannabis, with anti-spasmodic, anti-Anxiety, anti-inflammatory, analgesic and other pharmacological effects.

cis-Isolimonenol - Upstream Downstream Industry

Raw Materials

Cyclohexanol, 1-methyl-4-(1-methylethenyl)-2-(phenylseleninyl)-, [1S-(1α,2β,4α)]- (9CI)
Cyclohexanol, 2-(dimethyloxidoamino)-1-methyl-4-(1-methylethenyl)-, (1S,2S,4R)-
Cyclohexanol, 2-(dimethylamino)-1-methyl-4-(1-methylethenyl)-, (1S,2S,4R)-
cis-(S)-4-Isopropenyl-1-methylcyclohexene 1,2-epoxide
(+)-LIMONENE OXIDE 97% MIXTURE OF CIS&
(+)-TRANS-LIMONENE 1,2-EPOXIDE
(+)-Dipentene

cis-Isolimonenol - Preparation

A synthesis process of (1S,4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol, which includes the following steps:

(1) add 1.2Kg( )-limonene, 12L dichloromethane and 185g sodium bicarbonate into a 20L three-mouth flask, cool to 0 ℃, then add 1.78Kg m-chloroperoxybenzoic acid in three batches, control the internal temperature within 5 ℃, add stirring reaction for 2 hours, then add 23% sodium sulfite aqueous solution for quenching, stir separation, and then wash the organic phase with 13% sodium sulf, the crude product of 1.38Kg was obtained (trans -1,2-epoxylimonene had 46% purity and super 100% yield; Cis -1,2-epoxylimonene: trans -1,2-epoxylimonene = 1:1).

(2) under the protection of nitrogen, mix 1.4Kg diphenyldiselenide and 13L anhydrous ethanol, cool to 8 ℃, add 400g sodium borohydride in batches within 10 ℃, stir for 1 hour, drop the above 1,2-epoxylimonene, heat up to 80 ℃ for reflux reaction for 4 hours after dripping; Stop the reaction and cool down to 6 ℃;

(3) Add anhydrous tetrahydrofuran 3.2L dropwise to the reaction system of step (2), and continue to add 30% hydrogen peroxide 1.17Kg dropwise at the above temperature. After the dropwise addition, the temperature is increased to 20°C and stirred for 6 hours; add water to stand and separate the liquid, the aqueous phase is extracted with n-hexane, the organic phase is combined and washed with 10% sodium carbonate aqueous solution, add ethanol to the concentrated solution, concentrate again, repeat the operation twice, cool down to 0-5 ℃, stir for 3 hours, filter to obtain filter cake, add the filter cake to 10L chloroform, heat to 62 ℃ for reflux reaction overnight, and then distill under reduced pressure to obtain (1S,4R)-1-methyl -4-(1-methyl vinyl)-2-cyclohexene -1-alcohol 582g (purity 80.8%,ee%99.2%,de%84.3%).

Last Update：2024-04-09 21:11:58

cis-Isolimonenol - Nature

storage conditions	Sealed in dry,2-8°C
acidity coefficient (pKa)	14.66±0.40(Predicted)

Last Update：2024-04-09 18:58:34

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CAS: 22972-51-6
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