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
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(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
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Safety

HS Code 
2906190090
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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.

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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
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(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

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

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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