99-48-9

Basic information

• Product Name: CARVEOL
• Synonyms: (-)-carveol,mixtureofisomers;1-Methyl-4-isopropenyl-6-cyclohexen-2-ol;2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-o;2-methyl-5-(1-methylethenyl)-2-Cyclohexen-1-ol;2-Methyl-5(1-methylethenyl)cyclohex-2-ene-1-ol;5-Isopropenyl-2-methyl-2-cyclohexen-1-ol;p-Mentha-1,8-dien-6-ol;p-Mentha-6,8-dien-2-ol, l-
• CAS NO: 99-48-9
• Molecular Formula: C10H16O
• Molecular Weight: 152.23
• EINECS: 202-757-4
• Mol File: 99-48-9.mol
• Article Data: 114

Chemical Properties

• Melting Point: 24-25 °C
• Boiling Point: 226-227 °C751 mm Hg(lit.)
• Flash Point: 209 °F
• Appearance: /
• Density: 0.958 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0117mmHg at 25°C
• Refractive Index: n20/D 1.496
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethyl Acetate (Slightly)
• PKA: 14.60±0.60(Predicted)
• Water Solubility: Partly soluble in water. Soluble in alcohol, ethanol and DMSO.
• BRN: 6269416
• CAS DataBase Reference: CARVEOL(CAS DataBase Reference)
• NIST Chemistry Reference: CARVEOL(99-48-9)
• EPA Substance Registry System: CARVEOL(99-48-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• RTECS: OS8400000
• TSCA: Yes
• Hazardous Substances Data: 99-48-9(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 99-48-9 differently. You can refer to the following data:
1. Clear colorless to slightly yellow liquid
2. Carveol has spearmint-like odor.

Occurrence

In small amounts, sometimes esterified, it has been reported present in caraway seeds, spearmint, orange juice, mango and eucalyptus oil.

Uses

Carveol, is a constituent of spearmint essential oil in the form of cis-(?)-carveol. It can be used as a fragrance ingredient, and as a flavor additive in the food industry. It is also found that its alpha-trans-dihydroxy derivative, possesses potent antiparkinsonian activity in animal models.

Definition

ChEBI: A limonene monoterpenoid that is cyclohex-2-en-1-ol substituted by a methyl group at position 2 and a prop-1-en-2-yl group at position 5.

Aroma threshold values

Detection: 4 ppm

Air & Water Reactions

Insoluble in water.

Synthesis

The various d-, l- and dl- (cis- and trans-, respectively) forms have been prepared synthetically and isolated by means of the dinitrobenzoates according to Amvers’ law. They are prepared by oxidation of limonene or, better, from carvone.

InChI:InChI=1/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10?/m1/s1

Upstream product

• 99-49-0 Carvone 
• 30808-80-1 trans-6-chloro-p-mentha-1,8-diene 
• 555-31-7 aluminum isopropoxide 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 
• 138-86-3 limonene. 
• 5989-54-8 (-)-(S)-limonene 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 5989-27-5 D-limonene 
• 31198-76-2 carvoxime 
• 97-42-7 carvyl acetate 
• 6485-40-1 (R)-Carvone 
• 67-63-0 isopropyl alcohol 
• 3917-59-7 L-trans-pinocarveol 
• 7785-70-8 (+)-α-pinene 

Downstream Products

• 31269-75-7 cis-(1R,5R)-5-isopropyl-2-methyl-2-cyclohexen-1-ol 
• 119784-70-2 5-<(-)carveylthio>-1-phenyl-1H-tetrazole 
• 119784-70-2 5-(5-Isopropenyl-2-methyl-cyclohex-2-enylsulfanyl)-1-phenyl-1H-tetrazole 
• 18383-49-8 carvone epoxide 
• 99-49-0 Carvone 
• 124665-22-1 6-Iodo-4-isopropenyl-1-methyl-cyclohexene 
• 20549-48-8 (+)-neodihydrocarveol 
• 6485-40-1 (R)-Carvone 
• 81780-74-7 (4R,6R)-4-acetoxy-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-one 
• 22567-15-3 p-menth-6-en-2,9-diol 
• 84453-40-7 (1R,5R₇RS)-(4,7-dimethyl-6-oxabicyclo[3.2.1]-oct-3-en-7-yl)methanol 
• 97-42-7 carvyl acetate 
• 138943-59-6 N-(5-Isopropenyl-2-methyl-cyclohex-2-enyl)-acetamide 
• 141621-59-2 (4R,6R)-6-(2-Bromo-1-ethoxy-ethoxy)-4-isopropenyl-1-methyl-cyclohexene 

Relevant articles and documents

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

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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.).

Chiral Imidazo[1,5- a]pyridine-Oxazolines: A Versatile Family of NHC Ligands for the Highly Enantioselective Hydrosilylation of Ketones

Herein we report the synthesis and application of a versatile class of N-heterocyclic carbene ligands based on an imidazo[1,5-a]pyridine-3-ylidine backbone that is fused to a chiral oxazoline auxiliary. The key step in the synthesis of these ligands involves the installation of the oxazoline functionality via a microwave-assisted condensation of a cyano-azolium salt with a wide variety of 2-amino alcohols. The resulting chiral bidentate NHC-oxazoline ligands form stable complexes with rhodium(I) that are efficient catalysts for the enantioselective hydrosilylation of structurally diverse ketones. The corresponding secondary alcohols are isolated in good yields (typically >90%) with good to excellent enantioselectivities (80-93% ee). The reported hydrosilylation occurs at ambient temperatures (40 °C), with excellent functional group tolerability. Even ketones bearing heterocyclic substituents (e.g., pyridine or thiophene) or complex organic architectures are hydrosilylated efficiently, which is discussed further in this report.