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(1alpha,2beta,5alpha)-5-(isopropyl)-2-methylcyclohexan-1-ol, also known as Linalool, is a natural organic compound that belongs to the terpene family. It is a colorless to pale yellow liquid with a strong, sweet, floral scent. Linalool is chiral and exists in two enantiomeric forms, with the (1alpha,2beta,5alpha)-isomer being the most common and naturally occurring one. It is widely found in various plants, including citrus fruits, mint, and other essential oils.

499-69-4

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499-69-4 Usage

Uses

Used in Flavor and Fragrance Industry:
Linalool is used as a key component in the flavor and fragrance industry due to its pleasant and versatile scent. It is commonly found in perfumes, colognes, and other fragrance products to provide a fresh, floral, and slightly sweet aroma.
Used in Cosmetics and Personal Care Products:
Linalool is also used in the cosmetics and personal care industry for its scent and potential calming effects. It is often added to products such as shampoos, soaps, lotions, and creams to enhance their fragrance and provide a soothing experience for the user.
Used in Pharmaceutical Industry:
Linalool has been studied for its potential medicinal properties, including its ability to act as an anti-inflammatory, analgesic, and antimicrobial agent. It is being investigated for its potential use in the development of new drugs and treatments for various health conditions.
Used in Food Industry:
Linalool is used in the food industry as a flavoring agent, particularly in the production of beverages, confectionery, and baked goods. Its sweet, floral scent adds a pleasant aroma and taste to these products, enhancing their overall appeal.
Used in Aromatherapy:
Linalool is a popular ingredient in aromatherapy due to its calming and relaxing effects. It is believed to help reduce stress, anxiety, and promote a sense of well-being when inhaled or applied topically.
Used in Insect Repellent Industry:
Linalool has been found to have insect-repellent properties, making it a potential candidate for use in the development of natural insect repellents to protect against mosquito bites and other insect-borne diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 499-69-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 9 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 499-69:
(5*4)+(4*9)+(3*9)+(2*6)+(1*9)=104
104 % 10 = 4
So 499-69-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H20O/c1-7(2)9-5-4-8(3)10(11)6-9/h7-11H,4-6H2,1-3H3/t8-,9-,10-/m1/s1

499-69-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (1R,2R,5R)-2-methyl-5-propan-2-ylcyclohexan-1-ol

1.2 Other means of identification

Product number -
Other names p-Menthan-2-ol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:499-69-4 SDS

499-69-4Relevant academic research and scientific papers

Simple H2-free hydrogenation of unsaturated monoterpenoids catalyzed by Raney nickel

Philippov, Alexey A.,Chibiryaev, Andrey M.,Martyanov, Oleg N.

, p. 380 - 381 (2019/08/20)

A series of monoterpenoids (citral, carvone, menthone, camphor) as well as cyclohexanone and hex-5-en-2-one were subjected to transfer hydrogenation with PriOH/Raney nickel system at 82 or 150 °C. Among monoterpenoids, citral and carvone underwent full conversion at 82 °C within 5 h.

P450-catalyzed regio- and stereoselective oxidative hydroxylation of disubstituted cyclohexanes: Creation of three centers of chirality in a single CH-activation event This paper is dedicated to the memory of Harry H. Wasserman

Ilie, Adriana,Agudo, Rubén,Roiban, Gheorghe-Doru,Reetz, Manfred T.

, p. 470 - 475 (2015/02/02)

Wild-type P450-BM3 is able to catalyze in a highly regio- and diastereoselective manner the oxidative hydroxylation of non-activated disubstituted cyclohexane derivatives lacking any functional groups, including cis- and trans-1,2-dimethylcyclohexane, cis- and trans-1,4-dimethylcyclohexane, and trans-1,4-methylisopropylcyclohexane. In all cases except chiral trans-1,2-dimethylcyclohexane as substrate, the single hydroxylation event at a methylene group induces desymmetrization with simultaneous creation of three centers of chirality. Certain mutants increase selectivity, setting the stage for future directed evolution work.

Radical chain reduction of alkylboron compounds with catechols

Villa, Giorgio,Povie, Guillaume,Renaud, Philippe

supporting information; experimental part, p. 5913 - 5920 (2011/06/16)

The conversion of alkylboranes to the corresponding alkanes is classically per-formed via protonolysis of alkylboranes. This simple reaction requires the use of severe reaction conditions, that is, treatment with a carboxylic acid at high temperature (>150 °C). We report here a mild radical procedure for the transformation of organoboranes to alkanes. 4-tert-Butylcatechol, a well-established radical inhibitor and antioxidant, is acting as a source of hydrogen atoms. An efficient chain reaction is observed due to the exceptional reactivity of phenoxyl radicals toward alkylboranes. The reaction has been applied to a wide range of organoboron derivatives such as B- alkylcatecholboranes, trialkylboranes, pinacolboronates, and alkylboronic acids. Furthermore, the so far elusive rate constants for the hydrogen transfer between secondary alkyl radical and catechol derivatives have been experimentally determined. Interestingly, they are less than 1 order of magnitude slower than that of tin hydride at 80 °C, making catechols particularly attractive for a wide range of transformations involving C-C bond formation.

Antimicrobial therapeutic compositions for oral and topical use

-

Page 7; 18, (2008/06/13)

The invention provides therapeutic antimicrobial compositions comprising natural phenolic compounds and essential oil alcohols and methods of use. The therapeutic antimicrobial compositions are useful to treat internal and external bacterial, fungal, and protozoan infections, as well as antibiotic resistant and secondary opportunistic infections.

Oxidoreduction between Cycloalkanols and Cycloalkanones in the Cultured Cells of Nicotiana tabacum. Simulation of the Time-courses in the Oxidation of (+)-Borneol and the Reduction of (-)-Carvomenthone

Suga, Takayuki,Izumi, Shunsuke,Hirata, Toshifumi,Hamada, Hiroki

, p. 425 - 428 (2007/10/02)

The time-courses in the oxidation of (+)-borneol and the reduction of (-)-carvomenthone in the cultured cells of Nicotiana tabacum were simulated on the basis of the permeability of 5- to 7-membered cycloalkanols and their corresponding cycloalkanones into the cultured cells and the 13C NMR chemical shifts of the carbonyl carbon of (+)-camphor which is the oxidation product of (+)-borneol and (-)-carvomenthone which is a substrate for the reduction, respectively.

Reduction of Organic Compounds with Rare-Earth Intermetallics Containing Absorbed Hydrogen

Imamoto, Tsuneo,Mita, Takeshi,Yokoyama, Masataka

, p. 5695 - 5699 (2007/10/02)

The hydrogenation of organic compounds with rare-earth intermetallic hydrides has been investigated.Alkynes,alkenes,aldehydes,ketones,nitriles,imines, and nitro compounds are hydrogenated in excellent yields with LaNi5H6 or LaNi4.5Al0.5H5 at 0-60 deg C.The present hydrogenation method has the following characteristic features. (1) The intermetallic compounds (alloys) are not poisoned by compounds containing an amino group or a halogen atom. (2) The alloys can be used repeatedly without decrease in activity. (3) The reaction conditions are mild, and selective hydrogenations of some organic functional groups can be achieved.The reaction mechanism of this hydrogenation is briefly discussed in terms of stereochemistry and H/D exchange reactions.

Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution

Young, David,Jones, Martin,Kitching, William

, p. 563 - 573 (2007/10/02)

cis- and trans-Carvotanacetols and -piperitols have been converted into the corresponding allylic chlorides, which were made to react with both trimethyltinlithium and triphenyltinlithium.The resulting allylic stannanes were characterized by 1H, 13C and 119Sn n.m.r. spectroscopy, which permitted assignment of the relative configurations.Triphenyltinlithium appears to react in a (substantially) concerted fashion with the (optically active) chloride from the carvotanacetols yielding an optically active stannane.The corresponding trimethylstannane is optically inactive.Substitution reactions (SE') with acid and sulfur dioxide (in chloroform) are preferentially γ-anti and specifically γ-syn respectively, in line with conclusions based on other cyclohex-2-enyl systems.

HYDROGENOLYSE EN PHASE LIQUIDE SUR Pd/C DES EPOXYDES DU CARVOMENTHENE ET DU LIMONENE

Accrombessi, G.,Geneste, P.,Olive, J.-L.,Pavia, A. A.

, p. 3135 - 3140 (2007/10/02)

Hydrogenolysis over Pd/C of cis and trans epoxides of carvomenthene and limonene give a mixture of hydrocarbons, secondary and tertiary alcohols, and ketones in proportions dependent upon the nature of the starting material.In the limonene epoxides, the extracyclic double bond plays an important role in the opening of the oxirane ring through a common unsaturated tertiary alcohol intermediate by double bond migration, hydrogenation of which leads to the products.For the carvomenthene epoxides the results are similar to those found in the 4-t-butyl series with competition between cis addition and trans addition of hydrogen.The presence of the isopropenyl group leads to slower reaction rates in comparison with t-butyl analogues.

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