110-93-0 Usage
Description
6-Methyl-5-hepten-2-one is a heptenone that is hept-5-en-2-one substituted by a methyl group at position 6. It is a volatile oil component of citronella oil, lemongrass oil, and palmarosa oil. It has a strong, fatty, green, citrus-like odor and a bittersweet taste reminiscent of pear. It is one of the main flavor volatiles of tomatoes and occurs in nature as a degradation product of terpenes. It is an important intermediate in the synthesis of terpenoids.
Uses
1. Used in Organic Synthesis:
6-Methyl-5-hepten-2-one is used as an intermediate in the synthesis of terpenoids, which are a large and diverse class of organic compounds produced by a variety of plants, particularly conifers, and are used extensively in the perfumery and flavor industries.
2. Used in Perfumery:
6-Methyl-5-hepten-2-one is used as a fragrance ingredient in the perfumery industry due to its strong, fatty, green, citrus-like odor.
3. Used in Flavoring:
6-Methyl-5-hepten-2-one is used as a flavoring agent in the food and beverage industry, providing green, vegetative, musty, apple, banana, and green bean-like taste characteristics.
4. Used in Synthesis of Thyrsiferyl 23-Acetate:
6-Methyl-5-hepten-2-one is used in the synthesis of thyrsiferyl 23-Acetate, which acts as an anti-leukemic inducer of apoptosis, contributing to its use in the pharmaceutical industry.
5. Used in Inexpensive Perfumes:
6-Methyl-5-hepten-2-one is used as a cost-effective ingredient in the production of inexpensive perfumes, offering a pleasant citrus-like scent.
6. Used in the Flavor and Fragrance Industry:
6-Methyl-5-hepten-2-one is used in the flavor and fragrance industry due to its strong, fatty, green, citrus-like odor and bittersweet taste reminiscent of pear.
7. Used in the Synthesis of Ionones:
6-Methyl-5-hepten-2-one is used as an intermediate in the synthesis of ionones, which are important compounds in the perfume and fragrance industry.
8. Used in the Synthesis of Target Compounds:
6-Methyl-5-hepten-2-one is used in the synthesis of target compounds such as (Z)and (E)-tagetone, which are major components of tagetes oil, and Solanone, which is one of the flavor-determining constituents of tobacco.
9. Used in the Synthesis of Pseudoionone:
6-Methyl-5-hepten-2-one is used in the synthesis of pseudoionone, an intermediate in the synthesis of ionones, which are used in the perfume and fragrance industry.
10. Used in the Flavor and Fragrance of Various Foods and Beverages:
6-Methyl-5-hepten-2-one is found in various natural sources such as lemongrass, palmarosa, lemon, citronella, vervain, geranium, Ocimum canum, Artemisia scoparia, Urtica dioica, apple, apricot, sweet and sour cherry, orange juice, citrus peel oils, bilberry, lingonberry, cranberry, guava, grapes, melon, peach, pear, raspberry, strawberry, blackberry, carrot, celery, tomato, potato, clove bud and leaf, ginger, peppermint oil, thymus, Gruyere cheese, butter, beef, hop oil, beer, cognac, cider, white wine, cocoa, tea, peanut oil, avocado, Arctic bramble, cloudberry, olive, passion fruit, plumcot, rose apple, marjoram, starfruit, mango, fig, rice, rice bran, quince, origanum, calamus, buckwheat, corn oil, wort, dried bonito, elderberry, cherimoya, kiwifruit, mountain papaya, endive, lemon balm, clary sage, nectarine, clam, Cape gooseberry, maté, German chamomile oil, mastic gum leaf oil, lime oil, and apple brandy. Its presence in these sources contributes to their unique flavors and fragrances.
Preparation
From oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2CO3, and subsequent
distillation and vacuum fractionation; from acetoacetic ester and methyl-buten-3-ol-2 with aluminum alcoholate in Carroll’s reaction
followed by pyrolysis of the ester
Synthesis Reference(s)
Tetrahedron Letters, 28, p. 4893, 1987 DOI: 10.1016/S0040-4039(00)96654-1Synthesis, p. 796, 1981 DOI: 10.1055/s-1981-29599
Flammability and Explosibility
Flammable
Safety Profile
Moderately toxic by
ingestion. A skin irritant. Flammable liquid
when exposed to heat, sparks, or flame.
When heated to decomposition it emits
acrid smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 110-93-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 110-93:
(5*1)+(4*1)+(3*0)+(2*9)+(1*3)=30
30 % 10 = 0
So 110-93-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3
110-93-0Relevant articles and documents
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Kachinski,J.L.C.,Salomon,R.G.
, p. 3235 - 3238 (1977)
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Nakai,T. et al.
, p. 4027 - 4030 (1975)
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Generation of norisoprenoid flavors from carotenoids by fungal peroxidases
Zelena, Kateryna,Hardebusch, Bjoern,Huelsdau, Baerbel,Berger, Ralf G.,Zorn, Holger
, p. 9951 - 9955 (2009)
To biotechnologlcally produce norisoprenoid flavor compounds, two extracellular peroxidases (MsP1 and MsP2) capable of degrading carotenoids were isolated from the culture supematants of the basidiomycete Marasmlus scorodonlus (garlic mushroom). The encod
CARROL REARRANGEMENT ON THE SURFACE OF CHROMATOGRAPHIC GRADE ALUMINA
Pogrebnoi, S. I.,Kalyan, Y. B.,Krimer, M. Z.,Smit, W. A.
, p. 4893 - 4896 (1987)
Thermolysis on the surface of AL2O3 is proposed as a mild and convenient preparative method for -sigmatropic Carrol rearrangement of acetoacetic esters of tertiary allyl alcohols into respective γ,δ-unsaturated ketones.
INVESTIGATION OF THE KINETICS OF THE SYNTHESIS OF METHYLHEPTENONE UNDER CONDITIONS OF HOMOGENEOUS ACID CATALYSIS
Avrutskii, M. M.,Miropol'skaya, M. A.,Romanyuk, M. G.,Tikhova, I. B.,Zakharova, N. I.,et al.
, p. 798 - 801 (1981)
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A simple and practical phase-separation approach to the recycling of a homogeneous metathesis catalyst
Michrowska, Anna,Gulajski, Lukasz,Grela, Karol
, p. 841 - 843 (2006)
The air stable asarone-derived Ru carbene 16, a robust olefin metathesis catalyst, can be easily separated after reaction by deposition on silica gel and reused up to nine times. This procedure provides products of excellent purity with low Ru content. The Royal Society of Chemistry 2006.
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Watanabe,S. et al.
, p. 848 - 849 (1973)
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Salinaro,R.F.,Berson,J.A.
, p. 7094 - 7095 (1979)
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THE CARROLL REARRANGEMENT ON THE SURFACE OF CHROMATOGRAPHIC ABSORBENTS
Smit, V. A.,Pogrebnoi, S. I.,Kal'yan, Yu. B.,Krimer, M. Z.
, p. 888 (1987)
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Two-carbons homologation of methyl ketones examplified for the synthesis of citral from 6-methyl-5-hepten-2-one
Valla, Alain,Cartier, Dominique,Laurent, Alain,Valla, Benoist,Labia, Roger,Potier, Pierre
, p. 1195 - 1201 (2003)
New facile syntheses of 3,7-dimethyl-octadien-2,6-al (citral) from homologation of 6-methyl-5-hepten-2-one are reported.
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Meinwald
, p. 1617,1620 (1955)
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Cole,Kapur
, p. 360,362 (1957)
Pd-Catalyzed Nazarov-Type Cyclization: Application in the Total Synthesis of β-Diasarone and Other Complex Cyclopentanoids
Singh, Bara,Bankar, Siddheshwar K.,Ramasastry
supporting information, 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
Method for preparing methyl heptenone
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Paragraph 0052-0071, (2020/03/09)
The invention discloses a method for preparing methyl heptanone. According to the method, 3-methyl-2-butene-1-ol and acetone undergoes a selective dehydrogenation coupling reaction under the action ofa rhodium catalyst, alkali and an optional assistant to generate methyl heptenone. Compared with the prior art, the method has the advantages that cheap and easily available 3-methyl-2-butene-1-ol and acetone are used as raw materials; the methyl heptenone with high additional value is prepared through a one-step reaction; and the method is high in atom utilization rate, low in generation of three wastes, mild in conditions and high in selectivity and yield.
A ruthenium complex compound for the selective hydrogenation of the dienone method
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Paragraph 0053-0055, (2019/07/04)
The invention provides a selective hydrogenation of ruthenium complex α, γ - unsaturated dienone method, and in particular relates to a method for using the hydrogen in the catalyst under the action of the α, γ - unsaturated dienone is reduced to the corresponding γ - unsaturated ketone of the method, the catalyst employed for ruthenium complex, a ruthenium precursor and the ligand in-situ prepared. Major advantage of this invention is characterized in that the catalyst is composed of metal precursor and the ligand in-situ prepared, simple operation, high catalyst activity; pyridine, quinoline nitrogen-containing aromatic heterocycle such as the adding of the poisoned medicinal preparation, effectively restraining the product γ - unsaturated ketone transition hydrogenation reaction, an excellent selectivity, the cost is low.