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

General Description

(-)-CIS-MYRTANOL is a chemical compound that is commonly used in the fragrance and flavor industry. It is a colorless liquid with a floral and woody odor, and is often added to perfumes, colognes, and other personal care products to impart a fresh and pleasant scent. (-)-CIS-MYRTANOL is also found in various fruits and plants, and is known for its refreshing and uplifting aroma. In addition to its use in the fragrance industry, (-)-CIS-MYRTANOL is also used as a flavoring agent in food and beverages, adding a sweet and fruity note to a variety of products. Overall, this chemical is valued for its aromatic and flavor-enhancing properties, making it a versatile and widely used ingredient in the production of scented and flavored 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

• 56246-58-3 β-pinene oxide 
• 19894-97-4 (1R)-Myrtenol 
• 601-74-1 (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylic acid 
• 64-17-5 ethanol 
• 33741-31-0 (1R,2S)-pinan-10-oic acid methyl ester 
• 6712-78-3 myrtenol 
• 64-19-7 acetic acid 
• 23727-16-4 myrtenal 
• 33741-30-9 methyl (1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylate 
• 18172-67-3 beta-pinene 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 1118071-19-4 2-chloromethyl-6,6-dimethylbicyclo[3.1.1]heptane 
• 127-91-3 (1R/S,5R/S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane 
• 177698-19-0 Beta-pinene 

Downstream Products

• 4764-14-1 (+/-)-Myrtanal 
• 4764-14-1 (+/-)-Isomyrtanal 
• 81510-28-3 (1R,2R,5R)-2-[2-(Diphenyl-phosphinoyl)-ethoxymethyl]-6,6-dimethyl-bicyclo[3.1.1]heptane 
• 81510-31-8 [2-((1R,2R,5R)-6,6-Dimethyl-bicyclo[3.1.1]hept-2-ylmethoxy)-ethyl]-diphenyl-phosphane 
• 29021-36-1 (1R)-10-Acetoxy-cis-pinan 
• 6588-78-9 [6,6-dimethylbicyclo[3.1.1]heptan-2-yl]methanethiol 
• 16750-96-2 trans-Myrtanyl-tosylat 
• 590410-99-4 (1R,2R,5R)-trans-myrtanyl tosylate 
• 4764-14-1 (-)-cis-myrtanal 
• 106753-59-7 1-Phenyl-ethanone O-((1S,2R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ylmethyl)-oxime 

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.