ChemicalBook > CAS DataBase List > (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol

Product Name
(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol
CAS No.
22972-51-6
Chemical Name
(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol
Synonyms
(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol;trans-Mentha-2,8-dien-1-ol;(1S,4R) 1-METHYL-4-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-OL;cis-Isolimonenol;8-DIEN-1-OL;4R)-P-MENTHA-2;CanbidiolImpurity2;Cinchocaine Monomer;Cannabidiol Impurity 2;(+) p-mentha-2,8-dien-1-ol
CBNumber
CB3670819
Molecular Formula
C10H16O
Formula Weight
152.23
MOL File
22972-51-6.mol
More
Less

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol Property

Boiling point:
69-70 °C(Press: 3 Torr)
Density 
0.9398
Flash point:
87.0±19.6 °C
storage temp. 
2-8°C
solubility 
Chloroform (Soluble), Methanol (Soluble)
pka
14.66±0.40(Predicted)
form 
Oil
color 
Colourless
optical activity
-0.11° (C=1.00 g/100ml, CHCL3)
Water Solubility 
4.2g/L
Stability:
Light Sensitive
InChI
InChI=1S/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3/t9-,10+/m0/s1
InChIKey
MKPMHJQMNACGDI-VHSXEESVSA-N
SMILES
[C@@]1(C)(O)CC[C@@H](C(C)=C)C=C1
LogP
2.82
More
Less

Safety

HS Code 
2906190090
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

More
Less

N-Bromosuccinimide Price

TRC
Product number
M320460
Product name
(1S,4R)-1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol
Packaging
500mg
Price
$460
Updated
2021/12/16
Apolloscientific
Product number
OR12641
Product name
(1S,4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Purity
98%
Packaging
1g
Price
$18
Updated
2021/12/16
SynQuest Laboratories
Product number
2403-1-00
Product name
(1S,4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Purity
97%
Packaging
1g
Price
$20
Updated
2021/12/16
ApexBio Technology
Product number
C6671
Product name
cis-Isolimonenol
Packaging
500mg
Price
$50
Updated
2021/12/16
Apolloscientific
Product number
OR12641
Product name
(1S,4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Purity
98%
Packaging
5g
Price
$64
Updated
2021/12/16
More
Less

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol Chemical Properties,Usage,Production

Uses

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol is an acetal reagent used in the synthesis of desoxy cannabidiols and THC (T293202) related psychoactive compounds. It is formed from (+)-Limonene using a photosynthesized O2 transfer.

Definition

ChEBI: (1S,4R)-p-Mentha-2,8-dien-1-ol is a p-menthane monoterpenoid.

Hazard

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol causes skin irritation and serious eye irritation. It may cause respiratory irritation.

Synthesis

1415961-21-5

22972-51-6

The 1S,2S,5R-N,N,2-trimethyl-2-hydroxy-5-isopropenylcyclohexylamine oxide (1.430 g, 6.7 mmol) was heated in a Kugelrohr oven at 180 °C under 1 mmHg vacuum until the solid residue completely disappeared. The yellow distillate (1.317 g) was collected and purified by fast chromatography (ether:hexane=2:3) to afford the target product (1S,4R)-1-methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol (0.752 g, 74% yield) as a colorless oil. the Rf value was 0.32 (ether:hexane=2:3); the specific optical rotation [α]D26: +60 (c=1.0, CHCl3), consistent with literature value [α]D23: +53.8 (CHCl3); IR spectrum (SeZn) showed absorption peaks: 3354 (medium, broad, O-H), 2967 (medium, C-H), 2935 (medium, CH), 2861 (medium, CH), 1644 (medium, C=C), 1105 (strong, CO), and 888 (strong, C=CH bent), 736 (strong, C=CH bent) cm-1; 1H NMR (500 MHz, CDCl3) chemical shift: δ 5.70 (1H, ddd, 3JH2-H3=10.0 Hz, 4JH2-H4=2.4 Hz, 4JH2-H6=1.4 Hz, H2), 5.65 (1H, ddd. 3JH3-H2=10.0 Hz, 3JH3-H4=2.4 Hz, 4JH3-H5=0.8 Hz, H3), 4.78 (1H, quin, 4JH9b-H10≈4JH9b-H4=1.6 Hz, H9b), 4.74 (1H, quin, 4JH9a-H10≈4JH9a-H4=0.88 Hz, H9a), 2.65 (1H, m, H4), 1.88-1.73 (2H, m, H5eq, H6eq), 1.73 (3H, s, H10), 1.66-1.51 (3H, m, H5ax, H6ax, OH), 1.29 (3H, s, H7) ppm; 13C NMR (125 MHz, CDCl3) chemical shift : 148.3 (C8), 134.1 (C2), 132.3 (C3), 110.7 (C9), 67.6 (C1), 43.6 (C4), 36.9 (C6), 29.6 (C7), 25.0 (C5), 21.0 (C10) ppm; low resolution mass spectra (GC-MS): m/z 152 (M+, 2%), 134 ( [M-H2O]+, 11%), 119 ([M-CH3-H2O]+, 32%), 91 (100%), 79 (37%), 77 (46%); Elemental analysis (C10H16O) Calculated values: C 78.90, H 10.59; Measured values: C 78.25, H 10.59, N < 0.05.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 1, p. 52 - 54

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol Suppliers

Canada 1 China 233 India 4 United Kingdom 2 United States 12 Global 252
Toronto Research Chemicals
Tel
--
Fax
--
Email
info@trc-canada.com
Country
Canada
ProdList
6038
Advantage
71
More
Less

View Lastest Price from (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol manufacturers

Xi an Biohorlden Industry Trade Co Ltd
Product
cis-Isolimonenol 22972-51-6
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
200 kg
Release date
2025-06-09
Guangzhou Tengyue Chemical Co., Ltd.
Product
(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol 22972-51-6
Price
US $2300.00-1500.00/kg
Min. Order
1kg
Purity
99% Purity (What/sapp: +86 18145728414)
Supply Ability
1000 Tons/Month
Release date
2023-06-30
Zhengzhou Anbu Chem Co.,Ltd
Product
(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol 22972-51-6
Price
US $0.00/KG
Min. Order
0.1KG
Purity
99%
Supply Ability
1000KGS
Release date
2023-06-13

22972-51-6, (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enolRelated Search:

trans-4-Aminocyclohexanemethanol N,N-DIETHYLBENZAMIDE 2-Methylindole Adenosine 3-METHYLSTYRENE VINYL PROPIONATE Methoxyethene (1R)-(+)-TRANS-ISOLIMONENE (4R)-1-METHYL-4-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-OL (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol

  • (1S,4R) 1-METHYL-4-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-OL
  • (+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL
  • 2-Cyclohexen-1-ol,1-Methyl-4-(1-Methylethenyl)-, (1S,4R)-
  • (1S,4R)-1-methyl-4-prop-1-en-2-ylcyclohex-2-en-1-ol
  • (1S,4R)-p-Menth-2,8-dien-1-ol
  • (1S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol
  • (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol22972-51-6
  • (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol
  • trans-Mentha-2,8-dien-1-ol
  • (1S,4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-eno
  • (1S,4R)-4-Isopropenyl-1-methylcyclohex-2-en-1-ol
  • (1S,4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol 97+%
  • (1S,4R)-1-Methyl-4-(1-propen-2-yl)-2-cyclohexenol
  • cis-Isolimonenol
  • (+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL ISO 9001：2015 REACH
  • 4R)-P-MENTHA-2
  • 8-DIEN-1-OL
  • (+) p-mentha-2,8-dien-1-ol
  • CanbidiolImpurity2
  • Benzenemethanol,α-(aminomethyl)-7-bromo-
  • Milbemycin oxime 129496-10-2
  • 2-Cyclohexen-1-ol,1-methyl-4-(1-methylethenyl)-, (1S,4R)- (Menthadienol)
  • Cannabidiol Impurity 2
  • Cinchocaine Monomer
  • (1S,4R)-1 methyl-4-(prop-1 -en-2-yl)cylclohex-2-enol
  • (+)-cis-p-Mentha-2,8-dien-1-ol
  • (1S,4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol/cis-Isolimonenol
  • Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol
  • (+)-(1S,4R)-p-Mentha-2,8-dien-1-ol -
  • 1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol
  • 22972-51-6