20307-86-2

Basic information

• Product Name: (-)-Carveol
• Synonyms: p-Mentha-6,8-dien-2-ol; Carveol; 1-Methyl-4-isopropenyl-6-cyclohexen-2-ol; 2-06-00-00102 (Beilstein Handbook Reference); 2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-; 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol; 2-Methyl-5-isopropenyl-2-cyclohexen-1-ol; 5-Isopropenyl-2-methyl-2-cyclohexen-1-ol; AI3-27596; BRN 1861032; CCRIS 6219; EINECS 202-757-4; FEMA No. 2247; NSC 68313; UNII-1L9KXT85R9; p-Mentha-1,8-dien-6-ol; p-Mentha-1(6),8-dien-2-ol; 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol; (1S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol; (1R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol; (5R)-2-methyl-5-(1-methylethenyl)cyclohex-2-en-1-ol
• CAS NO: 20307-86-2
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.2334
• EINECS: 202-757-4
• Mol File: 20307-86-2.mol
• Article Data: 231

Chemical Properties

• Boiling Point: 231.5°C at 760 mmHg
• Flash Point: 91.2°C
• Density: 0.949g/cm³
• Vapor Pressure: 0.0117mmHg at 25°C
• Refractive Index: 1.497
• CAS DataBase Reference: (-)-Carveol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Carveol(20307-86-2)
• EPA Substance Registry System: (-)-Carveol(20307-86-2)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 20307-86-2(Hazardous Substances Data)

Upstream product

• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 99-49-0 Carvone 
• 6485-40-1 (R)-Carvone 
• 5989-54-8 (-)-(S)-limonene 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 
• 25488-94-2 (1S,2S,4R,6S)-2,7,7-trimethyl-3-oxatricyclo [4.1.1.02,4]octane 
• 555-31-7 aluminum isopropoxide 
• 5989-27-5 D-limonene 
• 7785-70-8 (+)-α-pinene 
• 130814-75-4 (-)-{1-(R)-[(1E)-2-methylbuta-1,3-dienyloxy]ethyl}benzene 
• 78-79-5 isoprene 
• 136476-14-7 [(S)-2,2-Dimethyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene 
• 175522-76-6 [(R)-2,2-Dimethyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene 
• 136476-12-5 [(S)-2-Methyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene 

Downstream Products

• 56169-11-0 (-)-α-phellandrene 
• 79055-08-6 (+/-)-O-(4-Nitro-benzoyl)-trans-carveol 
• 22567-15-3 p-menth-6-en-2,9-diol 
• 913815-72-2 C₁₆H₃₀OSi 
• 57429-67-1 (+/-)-O-(3.5-dinitro-benzoyl)-cis-carveol 
• 1423157-23-6 (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enyl 4-((E)-2-nitrovinyl)benzoate 

Relevant articles and documents

Chemoselective Transfer Hydrogenation of Flavoring Unsaturated Carbonyl Compounds over Zr and Hf-based Metal–Organic Frameworks

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Bu3SnH-catalyzed Barton-McCombie deoxygenation of alcohols [16]

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Tin-containing hydrotalcite-like compounds as catalysts for the Meerwein-Ponndorf-Verley reaction

Hydrotalcite-like compounds (HTs) containing Mg/Al or Mg/Al/Sn were prepared and used as precursors to obtain basic catalysts by calcination at 450 C. The catalysts were used in the Meerwein-Ponndorf-Verley (MPV) reaction of benzaldehyde and cyclohexanone in the presence of 2-propanol as hydrogen donor. The mixed oxide obtained by calcining the tin-containing HT was found to be more catalytically active than that obtained from the Mg/Al HT and the pure magnesium oxide. This result can be ascribed to the mechanism of the reaction, which involves acid-base sites on the catalyst surface. The most active catalyst was used in the MPV reactions of other carbonyl compounds including aldehydes and ketones with excellent conversion and selectivity.

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Photooxidation and phototoxicity of π-extended squaraines

This paper describes the synthesis of π-extended squaraines and their photooxidation properties and gives an in-depth characterization of these molecules as photosensitizing agents. Squaraines show a strong absorption in the tissue transparency window (600-800 nm), and upon irradiation, they undergo a photooxidation process, leading to the formation of peroxide and hydroperoxide radicals according to a type I radical chain process. Confocal laser microscopy demonstrates that the designed squaraines efficiently internalize in the cytoplasm and not in the nucleus of the cell. In the dark, they are scarcely cytotoxic, but after irradition, they promote a strong dose-dependent phototoxic effect in four different cancer cells. In HeLa and MCF-7 cells, squaraines 4 and 5, thanks to their hydrocarbon tails, associate to the membranes and induce lipid peroxidation, as indicated by a marked increase of malonyldialdehyde after photodynamic treatment, in agreement with in vitro photooxidation studies. FACS, caspase-3/7 assays and time-lapse microscopy demonstrate that the designed squaraines cause cell death primarily by necrosis.

Isomerization of α-pinene oxide in the presence of methyltrioxorhenium(VII)

The catalytic performance of methyltrioxorhenium(VII) (MTO) has been investigated for the first time in the isomerization of α-pinene oxide (PinOx) into campholenic aldehyde (CPA). The high isomerization activity of MTO is coupled with high selectivity to CPA: CPA yield of up to 87% (100% conversion) was obtained by using α,α,α-trifluorotoluene as solvent at 15 C. Catalyst recycling is possible in a relatively simple fashion by using MTO coupled to an appropriate ionic liquid. The catalytic application of MTO in the isomerization of PinOx versus the integrated epoxidation- isomerization process of the conversion of α-pinene into CPA is discussed.

Nickel-Catalyzed Arylation of C(sp3)-O Bonds in Allylic Alkyl Ethers with Organoboron Compounds

A nickel-catalyzed cross-coupling of allylic alkyl ethers with organoboron compounds through the cleavage of the inert C(sp3)-O(alkyl) bonds is described. Several types of allylic alkyl ethers can be coupled with various boronic acids or their derivatives to give the corresponding products in good to excellent yields with wide functional group tolerance and excellent regioselectivity. The gram-scale reaction and late-stage modification of biologically active compounds further prove the practicality of this synthetic method.

Pauson-Khand Reactions with Concomitant C?O Bond Cleavage for the Preparation of 5,5- 5,6- and 5,7-Bicyclic Ring Systems

Pauson-Khand reactions (PKR) with concomitant C?O bond cleavage have been developed for construction of 5,5- 5,6- and 5,7-bicyclic ring systems bearing complex stereochemistry. The chemistry generates intermolecular PKR-type products in an absolute regio- and stereochemical control which is hardly achievable through real intermolecular Pauson-Khand reactions. A mechanism for this Pauson-Khand reaction has been proposed based on deuterium labelling experiments. (Figure presented.).