51152-12-6

Basic information

• Product Name: (-)-CIS-MYRTANOL
• Synonyms: (6,6-Dimethylbicyclo[3.1.1]hept-2-yl)methanol;Bicyclo[3.1.1]heptane-2-methanol, 6,6-dimethyl-, [1S-(1alpha,2beta,5alpha)]-;(-)-CIS-MYRTANOL;10-PINANOL;(1S,2R)-6,6-DIMETHYLBICYCLO[3.1.1]HEPTANE-2-METHANOL;(1S,2R)-10-PINANOL;[1S-(1alpha,2beta,5alpha)]-6,6-dimethylbicyclo[3.1.1]heptane-2-methanol;(1S,2R)-10-Pinanol, (1S,2R)-6,6-Dimethylbicyclo[3.1.1]heptane-2-methanol
• CAS NO: 51152-12-6
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 257-018-9
• Mol File: 51152-12-6.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 127 °C22 mm Hg(lit.)
• Flash Point: 68 °C
• Appearance: /
• Density: 0.977 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0249mmHg at 25°C
• Refractive Index: n20/D 1.492
• Storage Temp.: 2-8°C
• PKA: 14.99±0.10(Predicted)
• CAS DataBase Reference: (-)-CIS-MYRTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-CIS-MYRTANOL(51152-12-6)
• EPA Substance Registry System: (-)-CIS-MYRTANOL(51152-12-6)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 51152-12-6(Hazardous Substances Data)

Usage

Description

(-)-CIS-MYRTANOL is a chemical compound that is widely used in the fragrance and flavor industry due to its colorless liquid form and floral, woody odor. It is known for its refreshing and uplifting aroma, which is often found in various fruits and plants.
Used in Fragrance Industry:
(-)-CIS-MYRTANOL is used as a fragrance ingredient for its fresh and pleasant scent, enhancing the aroma of perfumes, colognes, and other personal care products.
Used in Flavor Industry:
(-)-CIS-MYRTANOL is used as a flavoring agent in food and beverages for adding a sweet and fruity note, contributing to the overall taste and aroma of a variety of products.

InChI:InChI=1/C10H18O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h7-9,11H,3-6H2,1-2H3/t7-,8+,9-/m0/s1

Upstream product

• 23727-16-4 myrtenal 
• 6712-78-3 myrtenol 
• 1118071-19-4 2-chloromethyl-6,6-dimethylbicyclo[3.1.1]heptane 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 18172-67-3 beta-pinene 
• 33741-30-9 methyl (1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylate 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 33741-31-0 (1R,2S)-pinan-10-oic acid methyl ester 
• 601-74-1 (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylic acid 
• 56246-58-3 β-pinene oxide 
• 19894-97-4 (1R)-Myrtenol 
• 564-94-3 myrtenal 
• 1516933-90-6 2-(((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 4764-14-1 (+/-)-Myrtanal 
• 4764-14-1 (+/-)-Isomyrtanal 
• 29021-36-1 (1R)-10-Acetoxy-cis-pinan 
• 87727-48-8 myrtanyl tosylate 
• 81510-28-3 (1R,2R,5R)-2-[2-(Diphenyl-phosphinoyl)-ethoxymethyl]-6,6-dimethyl-bicyclo[3.1.1]heptane 
• 4764-14-1 cis-myrtanal 
• 127-92-4 6,6-Dimethyl-bicyclo<3.1.1>heptan 

Relevant articles and documents

Synthesis and Oxidation of Myrtanethiol and Its Functional Derivatives with Chlorine Dioxide

cis-Myrtanethiol and a mixture of diastereoisomeric myrtanethiols were synthesized starting from (-)-β-pinene. Their oxidation with chlorine dioxide afforded a number of derivatives such as disulfides, S-thiol-sulfonates, sulfonyl chlorides, and sulfonic acids. The effects of reaction conditions (solvent nature, reactant molar ratio, reaction time, catalyst) on the yield and ratio of the products were studied. The corresponding sulfonyl chloride was obtained in quantitative yield by oxidation of thiol in the presence of vanadyl acetyl-acetonate, and optimal conditions were found for quantitative formation of myrtanesulfonic acid.

A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides

A straightforward methodology for the synthesis of anti-Markovnikov-type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf)2 as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi-substituted internal and terminal epoxides, as well as a good functional-group tolerance. Various natural-product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate-to-excellent yields.

Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide

A simple and general visible-light-mediated oxidation of organoboron compounds has been developed with rose bengal as the photocatalyst, substoichiometric Et3N as the electron donor, as well as air as the oxidant. This mild and metal-free protocol shows a broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is demonstrated on the stereospecific aerobic oxidation of organoboron compounds.