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(R)-(-)-6-METHYL-5-HEPTEN-2-OL, also known as Sulcatol, is an organic compound with a distinct chemical structure characterized by its chiral center and functional groups. It is a colorless to pale yellow liquid with a strong, green, and woody odor. (R)-(-)-6-METHYL-5-HEPTEN-2-OL is known for its unique properties and applications in various industries.

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  • 1569-60-4 Structure
  • Basic information

    1. Product Name: (R)-(-)-6-METHYL-5-HEPTEN-2-OL
    2. Synonyms: 6-methyl-5-hepten-2-o;6-methylhept-5-en-2-ol;6-Methylhept-5-en-2-ol (Sulcatol);(R)-(-)-6-METHYL-5-HEPTEN-2-OL;(R)-6-METHYL-5-HEPTEN-2-OL;6-METHYL-5-HEPTEN-2-OL 99+%;5-Hepten-2-ol, 6-methyl-;(n)-6-methyl-5-hepten-2-ol
    3. CAS NO:1569-60-4
    4. Molecular Formula: C8H16O
    5. Molecular Weight: 128.21
    6. EINECS: 216-377-1
    7. Product Categories: Alcohols;Chiral Building Blocks;Organic Building Blocks;Alphabetical Listings;Flavors and Fragrances;M-N
    8. Mol File: 1569-60-4.mol
  • Chemical Properties

    1. Melting Point: -31.5°C (estimate)
    2. Boiling Point: 78 °C14 mm Hg(lit.)
    3. Flash Point: 154 °F
    4. Appearance: /
    5. Density: 0.844 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.362mmHg at 25°C
    7. Refractive Index: n20/D 1.448(lit.)
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 15.25±0.20(Predicted)
    11. Water Solubility: Soluble in Chloroform. Not miscible with water.
    12. BRN: 1720073
    13. CAS DataBase Reference: (R)-(-)-6-METHYL-5-HEPTEN-2-OL(CAS DataBase Reference)
    14. NIST Chemistry Reference: (R)-(-)-6-METHYL-5-HEPTEN-2-OL(1569-60-4)
    15. EPA Substance Registry System: (R)-(-)-6-METHYL-5-HEPTEN-2-OL(1569-60-4)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 40-67-36/37/38
    3. Safety Statements: 36/37-24/25-23
    4. WGK Germany: 3
    5. RTECS:
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1569-60-4(Hazardous Substances Data)

1569-60-4 Usage

Uses

Used in Chemical Synthesis:
(R)-(-)-6-METHYL-5-HEPTEN-2-OL is used as a key intermediate in the synthesis of various organic compounds, particularly in the fragrance and flavor industries. Its unique structure and functional groups make it a versatile building block for creating a wide range of molecules with diverse applications.
Used in Fragrance Industry:
(R)-(-)-6-METHYL-5-HEPTEN-2-OL is used as a fragrance ingredient for its strong, green, and woody odor. It is employed in the formulation of perfumes, colognes, and other scented products to provide a natural and complex aroma profile.
Used in Flavor Industry:
(R)-(-)-6-METHYL-5-HEPTEN-2-OL is used as a flavoring agent in the food and beverage industry. Its unique taste and aroma characteristics make it suitable for enhancing the flavor of various products, such as beverages, confectionery, and savory items.
Used in Pheromone Synthesis:
(R)-(-)-6-METHYL-5-HEPTEN-2-OL is used as a key component in the synthesis of aggregation pheromones for the ambrosia beetle, an insect pest of harvested timber in the Pacific North Coast. This application helps in the development of pest control strategies and the protection of timber resources.
Used in Pharmaceutical Industry:
(R)-(-)-6-METHYL-5-HEPTEN-2-OL has potential applications in the pharmaceutical industry due to its unique chemical structure and properties. It may be used as a starting material for the development of new drugs or as a component in drug delivery systems.

Check Digit Verification of cas no

The CAS Registry Mumber 1569-60-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,6 and 9 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1569-60:
(6*1)+(5*5)+(4*6)+(3*9)+(2*6)+(1*0)=94
94 % 10 = 4
So 1569-60-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O/c1-7(2)5-4-6-8(3)9/h5,8-9H,4,6H2,1-3H3/t8-/m1/s1

1569-60-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L09181)  (±)-6-Methyl-5-hepten-2-ol, 98%   

  • 1569-60-4

  • 5g

  • 266.0CNY

  • Detail
  • Alfa Aesar

  • (L09181)  (±)-6-Methyl-5-hepten-2-ol, 98%   

  • 1569-60-4

  • 25g

  • 979.0CNY

  • Detail
  • Aldrich

  • (195871)  6-Methyl-5-hepten-2-ol  99%

  • 1569-60-4

  • 195871-25G

  • 1,310.40CNY

  • Detail

1569-60-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name sulcatol

1.2 Other means of identification

Product number -
Other names 6-Methyl-5-hepten-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:1569-60-4 SDS

1569-60-4Relevant articles and documents

2,6,10-TRIMETHYL-7-(3-METHYLBUTYL)-DODECANE, A NOVEL SEDIMENTARY BIOLOGICAL MARKER COMPOUND.

Yon, D.A.,Maxwell, J.R.,Ryback, G.

, p. 2143 - 2146 (1982)

A C20 isoprenoid alkane (1) reported to occur in several recent sediments, has been isolated from Rozel Point crude oil and its structure confirmed by synthesis.

Carbon-13 NMR Spectra of Saturated Heterocycles. XI - Tetrahydropyrans (Oxanes)

Eliel, Ernest L.,Manoharan, Muthiah,Pietrusiewicz, K. Michal,Hargrave, Karl D.

, p. 94 - 107 (1983)

The 13C NMR spectra of 62 oxanes (tetrahydropyrans) with and without methyl substituents at various ring positions, some of them bearing in addition (or instead) ethyl, vinyl, ethynyl, carbomethoxy and methylol substituents at C-2, have been recorded, and the 294 resulting chemical shifts have been correlated by multiple linear regression analysis.Axial and equatorial α-, β-, γ-, δ-, gem- and vic-parameters for shifts caused by methyl groups at all ring positions, and similar parameters for Et, -CH=CH2, -CCH, CO2Me and CH2OH groups at C-2, are reported.Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and experimental shifts is excellent.This is probably the largest parameter set of this type extant. 13C NMR spectra of a number of additional substituted tetrahydropyrans, and of 3,6-dihydro-2H-pyrans and 3,4-dihydro-2H-pyrans, are tabulated and discussed.

Essential oil of aristolochia trilobata: Synthesis, routes of exposure, acute toxicity, binary mixtures and behavioral effects on leaf-cutting ants

De Oliveira, Bruna Maria S.,Melo, Carlisson R.,Alves, Péricles B.,Santos, Abra?o A.,Santos, Ane Caroline C.,Santana, Alisson Da S.,Araújo, Ana Paula A.,Nascimento, Pedro E. S.,Blank, Arie F.,Bacci, Leandro

, (2017)

Plants of the genus Aristolochia have been frequently reported as important medicinal plants. Despite their high bioactive potential, to date, there are no reports of their effects on leaf-cutting ants. Therefore, the present study aimed to evaluate the insecticidal activity of the essential oil of Aristolochia trilobata and its major components on Atta sexdens and Acromyrmex balzani, two species of leaf-cutting ants. The bioassays were performed regarding routes of exposure, acute toxicity, binary mixtures of the major components and behavioral effects. Twenty-five components were identified in the essential oil of A. trilobata using a gas chromatographic system equipped with a mass spectrometer and a flame ionization detector. The components found in higher proportions were sulcatyl acetate, limonene, p-cymene and linalool. The essential oil of A. trilobata and its individual major components were efficient against A. balzani and A. sexdens workers when applied by fumigation. These components showed fast and efficient insecticidal activity on ants. The components acted synergistically and additively on A. balzani and A. sexdens, respectively, and caused a strong repellency/irritability in the ants. Thus, our results demonstrate the great potential of the essential oil of A. trilobata and its major components for the development of new insecticides.

Oxone-KI Induced Lactonization and Etherification of Unsaturated Acids and Alcohols: A Formal Synthesis of Mintlactone

Curini, Massimo,Epifano, Francesco,Marcotullio, M. Carla,Montanari, Francesca

, p. 368 - 370 (2004)

Unsaturated acids and alcohols interact with Oxone and KI in acetonitrile-H2O and undergo iodolactonization and iodoetherification in short times with good yields. The reaction has been used for the formal synthesis of mintlactone starting from isopulegol.

Biocatalytic-Based Synthesis of Optically Pure (C-6)-Functionalized 1-(tert-Butyldimethylsilyloxy) 2-Methyl-(E)-2-heptenes

Liang, Shaowo,Paquette, Leo A.

, p. 445 - 452 (1990)

Controlled lipase hydrolysis of sulcatol chloroacetate at pH 7.2 to 55percent completion gives (R)-(-)-sulcatol of 89percent ee.Alkaline hydrolysis of the unreacted ester provides the (S)-(+) enantiomer efficiently and in an optically pure state.The latter is protected at its hydroxyl group, oxidized at its less sterically hindered terminal methyl group, and trans-formed into useful bifunctional reagents possessing 100percent ee.

Pd-Catalyzed Nazarov-Type Cyclization: Application in the Total Synthesis of β-Diasarone and Other Complex Cyclopentanoids

Singh, Bara,Bankar, Siddheshwar K.,Ramasastry

, p. 1043 - 1048 (2022/02/05)

We describe the palladium-catalyzed Nazarov-type cyclization of easily accessible (hetero)arylallyl acetates to pentannulated (hetero)arenes. This method provides ready access to various types of bi-, tri-, tetra-, and pentacyclic cyclopentanoids under ne

Amino Acid-Functionalized Metal-Organic Frameworks for Asymmetric Base–Metal Catalysis

Newar, Rajashree,Akhtar, Naved,Antil, Neha,Kumar, Ajay,Shukla, Sakshi,Begum, Wahida,Manna, Kuntal

supporting information, p. 10964 - 10970 (2021/03/29)

We report a strategy to develop heterogeneous single-site enantioselective catalysts based on naturally occurring amino acids and earth-abundant metals for eco-friendly asymmetric catalysis. The grafting of amino acids within the pores of a metal-organic framework (MOF), followed by post-synthetic metalation with iron precursor, affords highly active and enantioselective (>99 % ee for 10 examples) catalysts for hydrosilylation and hydroboration of carbonyl compounds. Impressively, the MOF-Fe catalyst displayed high turnover numbers of up to 10 000 and was recycled and reused more than 15 times without diminishing the enantioselectivity. MOF-Fe displayed much higher activity and enantioselectivity than its homogeneous control catalyst, likely due to the formation of robust single-site catalyst in the MOF through site-isolation.

Benzimidazole fragment containing Mn-complex catalyzed hydrosilylation of ketones and nitriles

Ganguli, Kasturi,Mandal, Adarsha,Sarkar, Bidisha,Kundu, Sabuj

supporting information, (2020/08/13)

The synthesis of a new bidentate (NN)–Mn(I) complex is reported and its catalytic activity towards the reduction of ketones and nitriles is studied. On comparing the reactivity of various other Mn(I) complexes supported by benzimidazole ligand, it was observed that the Mn(I) complexes bearing 6-methylpyridine and benzimidazole fragments exhibited the highest catalytic activity towards monohydrosilylation of ketones and dihydrosilylation of nitriles. Using this protocol, a wide range of ketones were selectively reduced to the corresponding silyl ethers. In case of unsaturated ketones, the chemoselective reduction of carbonyl group over olefinic bonds was observed. Additionally, selective dihydrosilylation of several nitriles were also achieved using this complex. Mechanistic investigations with radical scavengers suggested the involvement of radical species during the catalytic reaction. Stoichiometric reaction of the Mn(I) complex with phenylsilane revealed the formation of a new Mn(I) complex.

Base-free transfer hydrogenation of aryl-ketones, alkyl-ketones and alkenones catalyzed by an IrIIICp* complex bearing a triazenide ligand functionalized with pyrazole

Medrano-Castillo, Layla J.,Collazo-Flores, Miguel á.,Camarena-Díaz, Juan P.,Correa-Ayala, Erick,Chávez, Daniel,Grotjahn, Douglas B.,Rheingold, Arnold L.,Miranda-Soto, Valentín,Parra-Hake, Miguel

, (2020/03/13)

An IrIIICp* complex (2) bearing a triazenide ligand functionalized with pyrazole was synthesized and fully characterized by spectroscopic methods and the structure confirmed by X-ray diffraction studies. The catalytic activity of 2 and the control complex 3, which lacks of pyrazole in its structure, was evaluated in the reduction of aryl-ketones, alkyl-ketones, α,β-unsaturated and γ,δ-unsaturated ketones. The catalytic system, using either 2 or 3, exhibited good to excellent selectivity when tested with ketones and alkenones at 90 °C in 2-propanol as hydrogen source under base-free conditions. Reactivity of 2 in 2-propanol and NaH gave a neutral metal hydride (4) while in the absence of base gave two major cationic hydrides species (5 and 6).

Chemoselective Electrochemical Hydrogenation of Ketones and Aldehydes with a Well-Defined Base-Metal Catalyst

Fokin, Igor,Siewert, Inke

, p. 14137 - 14143 (2020/10/12)

Hydrogenation reactions are fundamental functional group transformations in chemical synthesis. Here, we introduce an electrochemical method for the hydrogenation of ketones and aldehydes by in situ formation of a Mn-H species. We utilise protons and electric current as surrogate for H2 and a base-metal complex to form selectively the alcohols. The method is chemoselective for the hydrogenation of C=O bonds over C=C bonds. Mechanistic studies revealed initial 3 e? reduction of the catalyst forming the steady state species [Mn2(H?1L)(CO)6]?. Subsequently, we assume protonation, reduction and internal proton shift forming the hydride species. Finally, the transfer of the hydride and a proton to the ketone yields the alcohol and the steady state species is regenerated via reduction. The interplay of two manganese centres and the internal proton relay represent the key features for ketone and aldehyde reduction as the respective mononuclear complex and the complex without the proton relay are barely active.

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