(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
(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
Safety
- HS Code
- 2906190090
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.
N-Bromosuccinimide Price
- Product number
- M320460
- Product name
- (1S,4R)-1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol
- Packaging
- 500mg
- Price
- $460
- Updated
- 2021/12/16
- Product number
- 084692
- Product name
- (1S,4R)-4-Isopropenyl-1-methylcyclohex-2-en-1-ol
- Purity
- 97%
- Packaging
- 100g
- Price
- $965
- Updated
- 2021/12/16
- Product number
- 52301
- Product name
- 1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol
- Packaging
- 1g
- Price
- $1075
- Updated
- 2021/12/16
- Product number
- J95374
- Product name
- (1S,4R)-p-Mentha-2,8-dien-1-ol
- Packaging
- 100g
- Price
- $1350
- Updated
- 2021/12/16
- Product number
- 52301
- Product name
- 1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol
- Packaging
- 2.5g
- Price
- $2250
- Updated
- 2021/12/16
(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol Chemical Properties,Usage,Production
Uses
1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol 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.
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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View Lastest Price from (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol manufacturers
- 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
- 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
- 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