22422-34-0

Basic information

• Product Name: (1R,2R,3S,5R)-(-)-2,3-Pinanediol
• Synonyms: (1R,2R,3S,5R)-(-)-2,3-PINANEDIOL;(1R,2R,3S,5R)-2,3-PINANEDIOL;(1R,2R,3S,5R)-(-)-PINANEDIOL;[1R-(1ALPHA,2ALPHA,3ALPHA,5ALPHA)]-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTANE-2,3-DIOL;((1R-(1ALPHA,2BETA,3BETA,5ALPHA))-2,6,6-TRIMETHYLBICYCLO(3.3.1)HEPTANE-2,3-DIOL);(-)-2-HYDROXYISOPINOCAMPHEOL;(-)-2-Hydroxyisopinocampheol, [1R-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol;(1R,2R,3S,5R)-(-)-2,3-Pinanediol,98%
• CAS NO: 22422-34-0
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• Product Categories: Chiral Compounds
• Mol File: 22422-34-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 57-59 °C(lit.)
• Boiling Point: 101-102 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to very faint yellow/Liquid
• Density: 0.9409 (rough estimate)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.4494 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol, Toluene
• PKA: 14.68±0.60(Predicted)
• BRN: 2039144
• CAS DataBase Reference: (1R,2R,3S,5R)-(-)-2,3-Pinanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3S,5R)-(-)-2,3-Pinanediol(22422-34-0)
• EPA Substance Registry System: (1R,2R,3S,5R)-(-)-2,3-Pinanediol(22422-34-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 22422-34-0(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline solid

Uses

Different sources of media describe the Uses of 22422-34-0 differently. You can refer to the following data:
1. (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.
2. (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.

InChI:InChI=1/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8-,10+/m0/s1

Upstream product

• 7785-70-8 (+)-α-pinene 
• 80-56-8 rac-α-pinene 
• 7785-26-4 (-)-α-pinene 
• 80-56-8 Pinene 
• 60-29-7 diethyl ether 
• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 
• 22466-70-2 (1R,2S,5R)-6,6-dimethylspiro[bicycle[3.1.1]heptane-2,2’-oxiran]-3-one 

Downstream Products

• 473-72-3 (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid 
• 612835-98-0 (1R,2R,6S,8R)-4-(Dimethyl-phenyl-silanyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 948854-88-4 C₁₉H₂₅NO₄ 
• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 
• 90473-01-1 (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate 

Relevant articles and documents

Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J

The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki-Miyaura cross-coupling and a Julia-Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.

-

-

A Modular Approach to the Asymmetric Synthesis of Cytisine

The asymmetric synthesis of (+)-and (-)-cytisine starts with Matteson homologations for the construction of a chiral C3-building block. Conversion of the C3-building block into a dihydropyridone is achieved by straightforward functional group interconversions and ring closing metathesis. After bromination, this central building block was diastereospecifically converted into cytisine in five steps.

Synthetic method of chiral vicinal diol and product thereof

The invention provides a synthetic method of chiral vicinal diol, which comprises the following steps: (1) adding alkene used as a precursor of the chiral vicinal diol and dichloromethane into a reaction device, adding alkali, and then at a temperature of minus 50 DEG C to minus 15 DEG C, adding a phase-transfer catalyst and then adding potassium permanganate or sodium permanganate in batches to perform a reaction so as to obtain an intermediate a; (2) adding the intermediate a into the reaction device, adding ethyl ether and petroleum ether with stirring, then adding boric acid in batches, and dropwise adding aqueous solution of potassium hydroxide to perform a reaction so as to obtain an intermediate b; (3) adding the intermediate b into the reaction device, adding ethyl ether and water, and then under the ice bath cooling condition, dropwise adding hydrofluoric acid, and stirring overnight at a low temperature to obtain the chiral vicinal diol. According to the synthetic method provided by the invention, the potassium permanganate or the sodium permanganate which is cheap, has low toxicity and pollutes the environment a little is used as a reaction reagent, and industrial synthetic production of a chiral vicinal diol compound is achieved.