(1R,2R,3S,5R)-(-)-2,3-Pinanediol

Base Information

• Chemical Name: (1R,2R,3S,5R)-(-)-2,3-Pinanediol
• CAS No.: 22422-34-0
• Molecular Formula: C10H18O2
• Molecular Weight: 170.252
• Hs Code.: 29061990
• European Community (EC) Number: 686-181-2
• UNII: R58L0W3A75
• DSSTox Substance ID: DTXSID9058733
• Nikkaji Number: J803.685C
• Wikidata: Q27287811
• ChEMBL ID: CHEMBL4303395
• Mol file: 22422-34-0.mol

Synonyms:2,3-Pinanediol,(1R,2R,3S,5R)- (8CI);Bicyclo[3.1.1]heptane-2,3-diol, 2,6,6-trimethyl-, [1R-(1a,2a,3a,5a)]-;(-)-(1R:2R:3S:5R)-cis-a-Pineneglycol;(-)-2,3-Pinanediol;(-)-cis-Pinane-cis-2,3-diol;(1R,2R,3S,5R)-(-)-Pinanediol;cis-a-Pinene glycol;

Chemical Property of (1R,2R,3S,5R)-(-)-2,3-Pinanediol

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 57-59 °C(lit.)
• Refractive Index: 1.52
• Boiling Point: 263.738 °C at 760 mmHg
• PKA: 14.68±0.60(Predicted)
• Flash Point: 120.838 °C
• PSA: 40.46000
• Density: 1.091 g/cm³
• LogP: 1.16430
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol, Toluene
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 170.130679813
• Heavy Atom Count: 12
• Complexity: 212

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1R,2R,3S,5R)-(-)-2,3-Pinanediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CC1C(C(C2)O)(C)O)C
• Isomeric SMILES: C[C@]1([C@@H]2C[C@@H](C2(C)C)C[C@@H]1O)O
• Uses: (1R,2R,3S,5R)-(-)-2,3-Pinanediol is a bicyclic monoterpene diols that has been shown to induce differentiation of S91 melanoma and PC12 pheochromocytoma cells and thus provide possible therapeutic and sunless tanning use. (1R,2R,3S,5R)-(-)-2,3-Pinanediol is a microbial oxidation product of (-)-β-pinene, a flavor and fragrance monoterpene. (1R,2R,3S,5R)-(-)-2,3-Pinanediol is a bicyclic monoterpene diols that has been shown to induce differentiation of S91 melanoma and PC12 pheochromocytoma cells and thus provide possible therapeutic and sunless tanning use. (1R,2R,3S,5R)-(-)-2,3-Pinanediol is a microbial oxidation product of (-)-β-pinene, a flavor and fragrance monoterpene.

Technology Process of (1R,2R,3S,5R)-(-)-2,3-Pinanediol

There total 15 articles about (1R,2R,3S,5R)-(-)-2,3-Pinanediol 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: 92.9%

Pinene (80-56-8,177698-18-9,25766-18-1) → (1R,2R,3S,5R)-2,3-pinane diol (22422-34-0)

Guidance literature:

With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide; water; In tert-butyl alcohol; for 24h; Reflux;

DOI:10.1021/jm9005093

Reference yield: 88.0%

(r)-pinanediol cyclohexylboronate → (1R,2R,3S,5R)-2,3-pinane diol (22422-34-0)

Guidance literature:

With hydrogenchloride; methyllithium; In methanol; diethyl ether; at -15 ℃; for 0.5h; 3 h, 25 deg C;

DOI:10.1016/0022-328X(88)87067-0

Reference yield: 85.0%

(-)-α-pinene (7785-26-4,25766-18-1) → (1R,2R,3S,5R)-2,3-pinane diol (22422-34-0)

Guidance literature:

With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide; In tert-butyl alcohol; for 20h; Inert atmosphere; Reflux;

upstream raw materials:

(-)-α-pinene

(1R,2S,5R)-6,6-dimethylspiro[bicycle[3.1.1]heptane-2,2’-oxiran]-3-one

(-)-(2R,3R,5R)-2-hydroxy-3-pinanone

diethyl ether

Downstream raw materials:

(1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid

(-)-(2R,3R,5R)-2-hydroxy-3-pinanone

(1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate

(1R,2R,3S,5R)-3-(benzyloxy)-pinanediol

Refernces

• 1、 Hobuss, Dennis,Thoene, Carsten,Laschat, Sabine,Baro, Angelika. "Synthesis of novel chiral bisphosphinites from α-pinene". . p. 2053 - 2056. Retrieved 2003.
• 2、 -. "Boric acid compounds, and preparation method and use thereof". Paragraph 0176; 0177; 0178. . Retrieved 2017/09/21.
• 3、 -. "Synthetic method of chiral vicinal diol and product thereof". Paragraph 0035-0036. . Retrieved 2017/05/26.