Perillyl alcohol

Base Information

• Chemical Name: Perillyl alcohol
• CAS No.: 536-59-4
• Deprecated CAS: 1406-56-0,66141-69-3,7644-38-4,66141-69-3
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Hs Code.: 29061990
• European Community (EC) Number: 208-639-9
• UNII: 319R5C7293
• DSSTox Substance ID: DTXSID4052180
• Nikkaji Number: J11.581I
• Wikipedia: Perillyl_alcohol
• Wikidata: Q15391928
• NCI Thesaurus Code: C1461
• Metabolomics Workbench ID: 134231
• ChEMBL ID: CHEMBL444711
• Mol file: 536-59-4.mol

Synonyms:(-)-p-mentha-1,8-dien-7-ol;(S)-perillyl alcohol;1-cyclohexene-1-methanol, 4-(1-methylethenyl)-, (4S)-;4-isopropenyl-cyclohex-1-ene-1-methanol;cyclohex-1-ene-1-methanol, 4(1-methylethenyl);dihydrocuminyl alcohol;NSC 641066;p-mentha-1,8-dien-7-ol;perilla alcohol;perilla alcohol, (R)-isomer;perilla alcohol, (S)-isomer;perillyl alcohol

Chemical Property of Perillyl alcohol

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.00628mmHg at 25°C
• Melting Point: 271-272 °C
• Refractive Index: n20/D 1.501(lit.)
• Boiling Point: 241.2°Cat760mmHg
• PKA: 14.85±0.10(Predicted)
• Flash Point: 99.6°C
• PSA: 20.23000
• Density: 0.94g/cm³
• LogP: 2.28130
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 179

Purity/Quality:

99%, ^*data from raw suppliers

(4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• Safety Statements: 26-39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC(=CC1)CO
• Recent ClinicalTrials: Safety and Efficacy Study in Recurrent Grade IV Glioma
• Description: p-Mentha-1,8-dien-7-ol has a characteristic odor similar to linalool and terpineol. The L-form is obtained starting from (3-pinene or by reducing perillic aldehyde with zinc dust and acetic acid, followed by saponification of the acetate.
• Uses: (4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol is used in preparation of perilla alcohol leaf alcohol carbonate as perfume. antineoplastic, apoptosis inducer; skin irritant, LD50(rat) 2100 mg/kg po

Technology Process of Perillyl alcohol

There total 57 articles about Perillyl alcohol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(4-isopropenyl-1-cyclohexen-1-yl)methyl acetate (15111-96-3) → perillol (536-59-4)

Guidance literature:

With water; sodium hydroxide; at 135 ℃; for 3h;

DOI:10.1007/s11164-012-0527-8

Reference yield: 94.0%

β-pinene oxide (6931-54-0) → 7-hydroxy-α-terpineol (5502-74-9) + perillol (536-59-4)

Guidance literature:

With deuteroperchloric acid; sodium sulfate; for 0.0833333h; Kinetics;

DOI:10.1021/acs.jpca.7b09427

Reference yield: 92.0%

trans-p-mentha-1(7),8-dien-2-ol → perillol (536-59-4)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; ammonium metavanadate; at 160 ℃; for 10h; Product distribution / selectivity; Inert atmosphere;

upstream raw materials:

perillaldehyde

D-limonene

β-pinene oxide

Beta-pinene

Downstream raw materials:

S-methyl S-isocarveyl dithiocarbonate

Dithiocarbonic acid O-(4-isopropenyl-cyclohex-1-enylmethyl) ester S-methyl ester

(s)-(-)-perillic acid

C₁₇H₂₅NO₃S

Refernces

• 1、 Li, Hui,Liu, Jian,Zhao, Juan,He, Huiting,Jiang, Dabo,Kirk, Steven Robert,Xu, Qiong,Liu, Xianxiang,Yin, Dulin. "Selective Catalytic Isomerization of β-Pinene Oxide to Perillyl Alcohol Enhanced by Protic Tetraimidazolium Nitrate". . p. 477 - 485. Retrieved 2021/05/04.
• 2、 -. "Method for synthesizing unsaturated primary alcohol in water phase". Paragraph 0036-0037. . Retrieved 2021/07/14.