| Identification | Back Directory | [Name]
(+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL | [CAS]
22972-51-6 | [Synonyms]
8-DIEN-1-OL
4R)-P-MENTHA-2
cis-Isolimonenol
trans-Mentha-2,8-dien-1-ol
(1S,4R)-p-Menth-2,8-dien-1-ol
(+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL
(1S,4R)-4-Isopropenyl-1-methylcyclohex-2-en-1-ol
(1S,4R)-1-Methyl-4-(1-propen-2-yl)-2-cyclohexenol
(1S,4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-eno
(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol
(1S,4R)-1-methyl-4-prop-1-en-2-ylcyclohex-2-en-1-ol
(1S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol
(1S,4R) 1-METHYL-4-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-OL
(+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL ISO 9001：2015 REACH
2-Cyclohexen-1-ol,1-Methyl-4-(1-Methylethenyl)-, (1S,4R)-
(1S,4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol 97+%
(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol22972-51-6 | [EINECS(EC#)]
805-440-4 | [Molecular Formula]
C10H16O | [MDL Number]
MFCD08460036 | [MOL File]
22972-51-6.mol | [Molecular Weight]
152.23 |
| Chemical Properties | Back Directory | [Boiling point ]
69-70 °C(Press: 3 Torr) | [density ]
0.9398 | [Fp ]
87.0±19.6 °C | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Soluble), Methanol (Soluble) | [form ]
Oil | [pka]
14.66±0.40(Predicted) | [color ]
Colourless | [Optical Rotation]
-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 |
| Hazard Information | Back Directory | [Uses]
1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol( 22972-51-6) 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]
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 |
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