18680-27-8

Basic information

• Product Name: (1S,2S,3R,5S)-(+)-2,3-Pinanediol
• Synonyms: (+)-2-Hydroxyisopinocampheol, (1S,2S,3R,5S)-2,3-Pinanediol, (1S,2S,3R,5S)-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol, [1S-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol;(+)-2-Hydroxyisopinocampheol, (1S,2S,3R,5S)-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol;[1S-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol;(1S, 2S, 3R, 5S)-(+)Pinanediol (Bortezomib Intermediate);(1S,2S,3R,5S)-(+)-2;(+)-pinanendiol;cis-2,3-Pinandiol;(1S,2S,3R,5S)-(+)-Pinanediol, (1S,2S,3R,5S)-(+)-2,3-Dihydroxy-2,6,6-trimethylbicyclo[3.1.1]heptane
• CAS NO: 18680-27-8
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• EINECS: 1592732-453-0
• Product Categories: Chiral Compounds
• Mol File: 18680-27-8.mol
• Article Data: 19

Chemical Properties

• Melting Point: 57-59 °C(lit.)
• Boiling Point: 239.9°C (rough estimate)
• Flash Point: >230 °F
• Appearance: White to light beige/Crystalline Powder, Crystals or Mass
• 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 (Slightly), Toluene (Slightly)
• PKA: 14.68±0.60(Predicted)
• BRN: 1853591
• CAS DataBase Reference: (1S,2S,3R,5S)-(+)-2,3-Pinanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3R,5S)-(+)-2,3-Pinanediol(18680-27-8)
• EPA Substance Registry System: (1S,2S,3R,5S)-(+)-2,3-Pinanediol(18680-27-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 18680-27-8(Hazardous Substances Data)

Usage

Description

(1S,2S,3R,5S)-(+)-2,3-Pinanediol is a bicyclic monoterpene diol, which is a white to light beige crystalline powder or found in crystal form. It is known for its ability to induce differentiation of certain types of cells, such as S91 melanoma and PC12 pheochromocytoma cells.

Uses

Used in Pharmaceutical Industry:
(1S,2S,3R,5S)-(+)-2,3-Pinanediol is used as a therapeutic agent for its potential role in inducing differentiation of specific cancer cells, which could provide treatment options for melanoma and pheochromocytoma.
Used in Cosmetics Industry:
In the cosmetics industry, (1S,2S,3R,5S)-(+)-2,3-Pinanediol is used for sunless tanning applications, offering an alternative to traditional sun exposure for achieving a tanned appearance.
Used in Chemical Synthesis:
(1S,2S,3R,5S)-(+)-Pinanediol serves as a chiral reagent in the synthesis of homochiral α-hydroxyketones, which are important in the production of various pharmaceuticals and chemicals. It is also used in the resolution of prolineboronate esters, which are relevant in the field of asymmetric synthesis.
Used in Fragrance Industry:
(1S,2S,3R,5S)-(+)-2,3-Pinanediol is utilized in the transformation of isopinocampheol and caryophyllene oxide, which are compounds used in the creation of fragrances and perfumes.

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 
• 22553-34-0 (+)-2α-hydroxy-3α-tosyloxypinane 
• 917-64-6 methyl magnesium iodide 
• 22419-94-9 Acetic acid (1S,3R,5S)-6,6-dimethyl-2-oxo-bicyclo[3.1.1]hept-3-yl ester 
• 917-54-4 methyllithium 
• 1845-25-6 (1S,2S,5S)-(-)-2-hydroxypinan-3-one 
• 29333-13-9 Acetic acid (1S,2S,5S)-2,6,6-trimethyl-3-oxo-bicyclo[3.1.1]hept-2-yl ester 
• 29333-20-8 (1S,3R,5S)-3-Benzyloxy-6,6-dimethyl-bicyclo[3.1.1]heptan-2-one 
• 74-88-4 methyl iodide 
• 1196-00-5 (-)-isopinocampheol 
• 84110-38-3 (1S,2S,3R,5S)-2α,3α-pinanediol methylboronic ester 
• 5057-98-7 cis-1,2-cyclopentanediol 
• 74481-29-1 2-(2-methoxyethyl)-6,6-dimethylbicyclo[3.1.1]heptane-cis-2,3-diol 
• 5447-67-6 (1SR,2RS)-1-methyl-cyclopentane-1,2-diol 

Downstream Products

• 1845-25-6 (1S,2S,5S)-(-)-2-hydroxypinan-3-one 
• 132488-71-2 pinanediol vinylboronic ester 
• 165881-36-7 (+)-pinanediol-4-bromo-butane-1-boronate 
• 302584-86-7 (1S,2S,3R,5S)-2-hydroxy-3-pinanyl p-styrenesulfonate 
• 76110-78-6 (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole 
• 616227-06-6 2-aminophenylboronic acid (+)-pinanediol ester 
• 84110-34-9 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole 
• 476335-09-8 (1S,2S,6R,8S)-2,9,9-Trimethyl-4-pentyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 244782-33-0 (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-(2-phenylethyl)hexahydro-4,6-methano-1,3,2-benzodioxaborole 
• 476334-35-7 (1S,2S,6R,8S)-2,9,9-Trimethyl-4-(3-phenyl-propyl)-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 476334-39-1 (1S,2S,6R,8S)-2,9,9-Trimethyl-4-(4-phenyl-butyl)-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 476334-87-9 (1S,2S,6R,8S)-4-[2-(4-Methoxy-phenyl)-ethyl]-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 497258-60-3 (+)-pinanediol 3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenylboronate 
• 476334-53-9 (1S,2S,6R,8S)-2,9,9-Trimethyl-4-(2-p-tolyl-ethyl)-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 

Relevant articles and documents

Synthesis of Thrombin Inhibitor DuP 714

The asymmetric synthesis of thrombin inhibitor DuP 714 (1) is described.The route uses the Matteson boronic ester homologation to prepare the key intermediate, α-aminoboronic acid 4.New methodology was developed for the formamidination of boroornithine peptides and for pinanediol boronate ester cleavage.

Discovery of novel 20S proteasome inhibitors by rational topology-based scaffold hopping of bortezomib

A series of structurally novel proteasome inhibitors 1–12 have been developed based rational topology-based scaffold hopping of bortezomib. Among these novel proteasome inhibitors, compound 10 represents an important advance due to the comparable proteasome-inhibitory activity (IC50 = 9.7 nM) to bortezomib (IC50 = 8.3 nM), the remarkably higher BEI and SEI values and the effectiveness in metabolic stability. Therefore, compound 10 provides an excellent lead suitable for further optimization.

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.