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Quality Control of cis-Isolimonenol Purity: 97% SDS Specification

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Product Details of cis-Isolimonenol

CAS No. :	22972-51-6
Formula :	C₁₀H₁₆O
M.W :	152.23
SMILES Code :	CC(=C)[C@@H]1CC[C@](C)(O)C=C1
Synonyms :	(1S,4R)-p-Mentha-2,8-dien-1-ol
MDL No. :	MFCD08460036
InChI Key :	MKPMHJQMNACGDI-VHSXEESVSA-N
Pubchem ID :	11105550

Safety of cis-Isolimonenol

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P264-P280-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of cis-Isolimonenol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 22972-51-6 ]

[ 22972-51-6 ] Synthesis Path-Downstream 1~38

1
[ 5989-27-5 ]
[ 52154-82-2 ]
[ 22972-51-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,2002,vol. 50,p. 1514 - 1516.
[2]Patent: GB761686,1954, .
[3]Justus Liebigs Annalen der Chemie,1964,vol. 674,p. 93 - 117.
[4]Justus Liebigs Annalen der Chemie,1964,vol. 674,p. 93 - 117.
[5]Patent: US3014047,1953, .

2
[ 52154-82-2 ]
[ 22972-51-6 ]
[ 111319-95-0 ]

References: [1]Bulletin de la Societe Chimique de France,1960,p. 37.
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1959,vol. 249,p. 306.

3
[ 39911-79-0 ]
[ 22972-51-6 ]
[ 39911-80-3 ]

References: [1]Helvetica Chimica Acta,1973,vol. 56,p. 519 - 524.

4
[ 22972-51-6 ]
[ 3901-95-9 ]

References: [1]Bulletin de la Societe Chimique de France,1960,p. 37 - 45.
[2]Roczniki Chemii,1963,vol. 37,p. 773 - 784.
[3]Justus Liebigs Annalen der Chemie,1964,vol. 674,p. 93 - 117.
[4]Journal of Organic Chemistry,1966,vol. 31,p. 1937 - 1945.

5
[ 504-15-4 ]
[ 22972-51-6 ]
[ 35482-50-9 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 1083 - 1086.

6
[ 504-15-4 ]
[ 22972-51-6 ]
[ 22972-64-1 ]

References: [1]Archiv der Pharmazie,1982,vol. 315,p. 551 - 561.

7
[ 67884-29-1 ]
[ 22972-51-6 ]
[ 120467-18-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1263 - 1270.

8
[ 58545-34-9 ]
[ 22972-51-6 ]
[ 58545-36-1 ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 2564 - 2571.

9
[ 14531-52-3 ]
[ 22972-51-6 ]
[ 120467-12-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1263 - 1270.

10
[ 14531-52-3 ]
[ 22972-51-6 ]
[ 120467-11-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1263 - 1270.

11
[ 14531-52-3 ]
[ 22972-51-6 ]
[ 120467-09-6 ]
[ 120467-10-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1263 - 1270.

12
[ 41408-15-5 ]
[ 22972-51-6 ]
[ 1972-05-0 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 1083 - 1086.

13
[ 71186-11-3 ]
[ 22972-51-6 ]
[ 57704-21-9 ]

References: [1]Helvetica Chimica Acta,1980,vol. 63,p. 2508 - 2514.
[2]Journal of the Chemical Society. Perkin transactions I,1988,p. 1255 - 1262.

14
[ 71186-11-3 ]
[ 22972-51-6 ]
[ 57704-22-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1255 - 1262.

15
[ 71186-11-3 ]
[ 22972-51-6 ]
[ 74333-69-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1255 - 1262.

16
[ 71186-11-3 ]
[ 22972-51-6 ]
[ 74333-68-9 ]
[ 74333-67-8 ]
[ 120467-27-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1255 - 1262.

17
[ 5989-27-5 ]
[ 99-48-9 ]
[ 18383-51-2 ]
[ 52154-82-2 ]
[ 22972-51-6 ]
[ 2102-62-7 ]
[ 10374-04-6 ]

References: [1]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 1944 - 1949.
[2]Archiv der Pharmazie,1988,vol. 321,p. 385 - 389.
[3]Journal of Organic Chemistry,1994,vol. 59,p. 1135 - 1138.

18
[ 22972-51-6 ]
[ 77523-20-7 ]
methyl 4"(R,S)-methyl-Δ¹⁽⁶⁾-tetrahydrocannabinol-5"-oate [ No CAS ]

References: [1]Helvetica Chimica Acta,1980,vol. 63,p. 2508 - 2514.

19
[ 22972-51-6 ]
[ 61187-22-2 ]

References: [1]Helvetica Chimica Acta,1980,vol. 63,p. 76 - 94.

20
[ 22972-51-6 ]
(+)-(1'R,4'S)-1-(4'-hydroxy-4'-methyl-2'-cyclohexen-1'-yl)ethanone [ No CAS ]

References: [1]Helvetica Chimica Acta,1980,vol. 63,p. 76 - 94.

21
[ 22972-51-6 ]
[ 56469-10-4 ]
[ 97452-63-6 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 1083 - 1086.

22
[ 22972-51-6 ]
[ 60526-81-0 ]
[ 97452-60-3 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 1083 - 1086.

23
[ 22972-51-6 ]
[ 58016-28-7 ]
[ 16850-65-0 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 2935 - 2938.

24
[ 22972-51-6 ]
[ 74356-41-5 ]
[ 63998-82-3 ]
[ 120467-25-6 ]
[ 120467-26-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1255 - 1262.

25
[ 22972-51-6 ]
[ 120467-32-5 ]
[ 120467-33-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1255 - 1262.

26
[ 74756-11-9 ]
[ 22972-51-6 ]

Yield	Reaction Conditions	Operation in experiment
512 g	In chloroform; at 62℃; for 6h;Inert atmosphere;	(3) Add 3.8 L of anhydrous tetrahydrofuran to the system of the step (2), and continue to add 630 g of 30% hydrogen peroxide at the above temperature. After the completion of the dropwise addition, the temperature is raised to 20 C, and stirred for 6 hours; The aqueous phase is extracted with n-hexane, and the organic phase is combined, washed with a 10% aqueous sodium carbonate solution, brine, and concentrated to remove organic solvent. Add ethanol to the concentrate, concentrate again, repeat the operation twice and then cool to 3 C. After stirring for 3 hours, the filter cake was filtered, and the filter cake was added to 6 L of chloroform. The mixture was heated to 62 C, refluxed overnight, and then distilled under reduced pressure to give trans-menthyl-2,8-dien-1-ol 512 g (purity 97.5%, ee% 99.2%, de%99.1%). The total yield of the reaction from the compound 2 (1,2-epoxylimonene) to the compound 5 (trans-menthyl-2,8-dien-1-ol) was calculated to be 67%. The total yield from the starting material 1 (limonene) to the compound 5 (trans-menthyl-2,8-dien-1-ol) was 38%.

References: [1]Australian Journal of Chemistry,1980,vol. 33,p. 451 - 454.
[2]Patent: CN109734554,2019,A .Location in patent: Paragraph 0034; 0039-0040; 0043-0045.

27
[ 22972-51-6 ]
[ 78-39-7 ]
[ 107602-58-4 ]

References: [1]Helvetica Chimica Acta,1986,vol. 69,p. 2026 - 2037.

28
[ 138-86-3 ]
[ 22972-51-6 ]

References: [1]Helvetica Chimica Acta,1980,vol. 63,p. 76 - 94.

29
[ 22972-51-6 ]
[ 108-46-3 ]
[ 29093-21-8 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 1083 - 1086.
[2]Helvetica Chimica Acta,1969,vol. 52,p. 1102 - 1134.

30
[ 22972-51-6 ]
[ 500-66-3 ]
[ 13956-29-1 ]
[ 22972-55-0 ]
[ 22972-53-8 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 1083 - 1086.

31
[ 5989-27-5 ]
[ 22972-51-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1965,vol. 687,p. 26 - 39.
[2]Tetrahedron Letters,2013,vol. 54,p. 52 - 54.
[3]Patent: CN109734554,2019,A .
[4]Patent: CN109734554,2019,A .

32
[ 22972-51-6 ]
[ 38862-65-6 ]
(-)-Cannabidiol-carbonsaeure-aethylester [ No CAS ]

References: [1]Helvetica Chimica Acta,1969,vol. 52,p. 1102 - 1134.

33
[ 22972-51-6 ]
[ 52154-82-2 ]

References: [1]Justus Liebigs Annalen der Chemie,1965,vol. 687,p. 26 - 39.

34
[ 22972-51-6 ]
[ 16750-82-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1965,vol. 687,p. 26 - 39.

35
(+)-trans-N_.N-Dimethylamino-2-p-menthen-8-ol-1-N-oxyd [ No CAS ]
[ 22972-51-6 ]

References: [1]Roczniki Chemii,1963,vol. 37,p. 773 - 784.

36
[ 22972-51-6 ]
[ 108-46-3 ]
[ 22972-73-2 ]

References: [1]Helvetica Chimica Acta,1969,vol. 52,p. 1102 - 1134.

37
[ 22972-51-6 ]
[ 108-46-3 ]
O 1848 [ No CAS ]

References: [1]Helvetica Chimica Acta,1969,vol. 52,p. 1102 - 1134.

38
[ 22972-51-6 ]
[ 500-66-3 ]
[ 13956-29-1 ]

Yield	Reaction Conditions	Operation in experiment
24%		Olivetol (920 mg, 0.00511 mol) and p-toluene sulfonic acid (PTSA) (110 mg, 0.000578 mol) were dissolved in benzene; the resulting reaction mixture azeotroped for 2.5 h. The reaction mixture was cooled to room temperature and under argon (+)-(1S,4R)-p-Mentha-2,8-dien-1-ol (586 mg, 0.00385 mol) was added and stirred at room temperature for 30 min. After completion of the reaction, the reaction mixture was diluted with diethyl ether and washed with saturated sodium bicarbonate solution. The organic layer separated and was dried on anhydrous sodium sulfate. The ether layer evaporated and purified on silica column by using petroleum ether and diethyl ether as eluent (98:2). Finally 300 mg of cannabidiol (300 mg) was collected (24percent).1HNMR (CDCl3): 6.23-6.41 (m,2H), 5.99 (s,1H,D2O exchangeable), 5.66 (s,1H), 4.56 (s,1H), 4.49 (bs,1H,D2O exchangeable) 4.46 (s,1H), 3.96 (m,1H), 2.00-2.47 (m,5H),1.87 (m,5H), 1.46-1.83 (m,6H), 1.23-1.48 (m,3H), 0.96-1.00 (m,3H).

References: [1]Patent: US2009/36523,2009,A1 .Location in patent: Page/Page column 12.
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 424 - 428.
[3]Helvetica Chimica Acta,1969,vol. 52,p. 1102 - 1134.

Historical Records

Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Halogenation • Heat of Combustion • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions of Amines • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

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CAS No.: 22972-51-6

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CAS No.: 22972-51-6

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Product Details of cis-Isolimonenol

Safety of cis-Isolimonenol

Application In Synthesis of cis-Isolimonenol

[ 22972-51-6 ] Synthesis Path-Downstream 1~38

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