57457-02-0

Basic information

• Product Name: [1S-(1alpha,3alpha,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol
• Synonyms: [1S-(1alpha,3alpha,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol;Einecs 260-745-4
• CAS NO: 57457-02-0
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.24872
• EINECS: 260-745-4
• Mol File: 57457-02-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 272.8°Cat760mmHg
• Flash Point: 126.6°C
• Appearance: /
• Density: 1.091g/cm³
• CAS DataBase Reference: [1S-(1alpha,3alpha,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: [1S-(1alpha,3alpha,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol(57457-02-0)
• EPA Substance Registry System: [1S-(1alpha,3alpha,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol(57457-02-0)

Safety Data

• Hazardous Substances Data: 57457-02-0(Hazardous Substances Data)

Usage

General Description

[1S-(1α,3α,4α,6α)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol, also known as menthol, is a naturally occurring compound found in mint plants such as peppermint and spearmint. It has a characteristic minty aroma and flavor and is widely used in various consumer products including food, beverages, pharmaceuticals, and personal care products. Menthol is known for its cooling and soothing properties and is commonly used as a topical analgesic to relieve minor aches and pains. In addition, it is also used as a flavoring agent in food and beverages and as a fragrance in cosmetics and personal care products. Menthol has been studied for its potential health benefits including its anti-inflammatory, antiviral, and antibacterial properties.

InChI:InChI=1/C10H18O2/c1-9(2)6-4-8(11)10(3,12)5-7(6)9/h6-8,11-12H,4-5H2,1-3H3

Upstream product

• 38228-33-0 4,5-Epoxycaran-trans-3-ol-acetat 
• 498-15-7 (+)-Δ³-carene 
• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 
• 13466-78-9 3-carene 
• 4017-82-7 (+)-trans-car-2-en-4-ol 
• 78-85-3 2-methylpropenal 
• 936-91-4 3-carene epoxide 
• 10309-63-4 (-)-Caran-3β,4β-diol-4-acetat 
• 73582-88-4 C₁₂H₁₈O₃ 
• 936-91-4 α-3,4-Epoxycarane 
• 936-91-4 (1S,3R,4S,6R)-3,4-epoxycarane 
• 43124-71-6 (+)-4α-acetoxy-2-carene 

Downstream Products

• 36482-69-6 (1R,4S,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one 
• 33116-78-8 (1S,3R)-(+)-3-hydroxy-4-isocaranyl tosylate 
• 10395-46-7 (+)-3α,4β-caranediol 
• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 
• 1266680-98-1 (3S,5aR,6aS,7aS)-3-benzyl-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 1266681-00-8 (3S,5aR,6aS,7aS)-3-(4-nitrobenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 1266681-01-9 (3S,5aR,6aS,7aS)-3-(4-bromobenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 1266681-16-6 (3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 58930-63-5 (3¹R,3³S)-3²,3²-dimethyl-3(1,3)cyclopropyla-5-oxohexanoic acid 
• 24348-06-9 (+)-3β-hydroxy-4-caranone 
• 1459202-31-3 C₁₀H₁₅ClO₂ 
• 22556-08-7 trans-3,4-caranediol 

Relevant articles and documents

Amine Catalysis for the Organocatalytic Diboration of Challenging Alkenes

The generation of in situ sp2–sp3diboron adducts has revolutionised the synthesis of organoboranes. Organocatalytic diboration reactions have represented a milestone in terms of unpredictable reactivity of these adducts. However, current methodologies have limitations in terms of substrate scope, selectivity and functional group tolerance. Here a new methodology based on the use of simple amines as catalyst is reported. This methodology provides a completely selective transformation overcoming current substrate scope and functional/protecting group limitations. Mechanistic studies have been included in this report.

Thiol-catalysed radical-chain redox rearrangement reactions of benzylidene acetals derived from terpenoid diols

The thiol-catalysed radical-chain redox rearrangement of cyclic benzylidene acetals derived from 1,2- and 1,3-diols of terpene origin has been investigated from both synthetic and mechanistic standpoints. The redox rearrangement was carried out either at ca. 70°C (using ButON=NOBut as initiator) or at ca. 130°C (using ButOOBut as initiator) in the presence of triisopropylsilanethiol or methyl thioglycolate as catalyst; the silanethiol was usually more effective. This general reaction affords the benzoate ester of the monodeoxygenated diol, unless rearrangement of intermediate carbon-centred radicals takes place prior to final trapping by the thiol to give the product, in which case structurally rearranged esters are obtained. For the benzylidene acetals of 1,2-diols prepared by vicinal ds-dihydroxylation of 2-carene, α-pinene or β-pinene, intermediate cyclopropylcarbinyl or cyclobutylcarbinyl radicals are involved and ring opening of these leads ultimately to unsaturated monocyclic benzoates. 1,2-Migration of the benzoate group in the intermediate p-benzoyloxyalkyl radical sometimes also competes with thiol trapping during the redox rearrangement of benzylidene acetals derived from 1,2-diols. Redox rearrangement of the benzylidene acetal from carane-3,4-diol, obtained by cis-dihydroxylation of 3-carene, does not involve intermediate cyclopropylcarbinyl radicals and leads to benzoate ester in which the bicyclic carane skeleton is retained. The inefficient redox rearrangement of the relatively rigid benzylidene acetal from exo,exo-norbornane-2,3-diol is attributed to comparatively slow chain-propagating β-scission of the intermediate 2-phenyl-1,3-dioxolan-2-yl radical, probably caused by the development of adverse angle strain in the transition state for this cleavage. Similar angle strain effects are thought to influence the regioselectivities of redox rearrangement of bicyclic [4.4.0]benzylidene acetals resulting from selected 1,3-diols, themselves prepared by reduction of aldol adducts derived from reactions of aldehydes with the kinetic lithium enolates obtained from menthone and from isomenthone.

Rhutenium-Catalyzed cis-Dihydroxylation of Alkenes: Scope and Limitations

Oxidative ruthenium catalysis (0.07 molequiv RuCl3*(H2O)3, 1.5 molequiv NaIO4, EtOAc/CH3CN/H2O 3:3:1), beyond the usual C-C bond cleavage to give dicarbonyls, have been shown to syn-dihydroxylate a wide range of alkenes (except for strained bicyclic alkenes, sterically hindered trisubstituted alkenes, and most tetrasubstituted alkenes) to give vicinal diols rapidly (within minutes) and efficiently.The minor products are the usual oxidative fission products, namely, ketones and aldehydes or carboxylic acids, and sometimes ketols.Longer reaction times lower the yields of most diols, probably owing to oxidative glycol cleavage.Reactions with substrates containing one or more electron-withdrawing groups in conjugation with or adjacent to the alkene moiety are generally slower but give better yields.The diastereoselectivity of the present "flash" dihydroxylation, anti to the existing α-stereogenic center, with cycloalkenes is excellent whereas that with acyclic alkenes is moderate to poor.Sodium metaperiodate is still the best co-oxidant for the catalytic reaction.Aqueous acetonitrile (approximately 86percent) as an alternative solvent system was found to give better yields of 1,2-diols than the original solvent system in some cases. - Keywords: alkenes, catalysis, dihydroxylations, electrophilicity, ruthenium compounds.