CAS number：541-91-3
molecular formula：C16H30O
molecular weight：238.41
EINECS number：208-795-8

English synonyms

MUSCONE;3-methylcyclopentadecan-1-one;3-methyl-cyclopentadecanon;FEMA 3434;DL-MUSCONE;3-METHYL-1-CYCLOPENTADECANONE;3-METHYL-CYCLOPENTADECANONE;Cyclopentadecanone, 3-methyl-

Related categories

Chemical Products-Organic Chemicals;Organic Chemical Raw Materials;Chemical Raw Materials-1;Fragrance;Chemical Raw Materials;Flavors and Fragrances;Traditional Chinese Medicine Standard Substances;Small Molecule Inhibitors,Natural Products;Chinese Medicine Reference Substances;Standards;Carbonyl Compounds;Reference Substances,Standard Substances ;plant extract;chemical reagent;pharmaceutical intermediate;reference substance;plant extract standard substance;small molecule inhibitor;Inhibitors;standard substance-traditional Chinese medicine standard substance;standard substance-traditional Chinese medicine standard substance;analytical reagent-reference substance;standard substance, control Product;organic and inorganic chemical industry;organic raw material;raw material;monomer fragrance;daily chemical;solid fragrance;chemical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract

Introduction

Musk ketone, scientific name 3-methylcyclopentadecanone, naturally produced L-form is a colorless liquid with a strong musk odor. Relative density 0.862. (17/4°C), melting point -19°C, boiling point 15°C (12×133.322Pa), refractive index 1.4776 (17°C). Natural musk ketone is one of the active ingredients extracted by distillation from the dried musk musk in the mature male sachet of Mosochus Bersxoxskii Fleror or the original musk deer Mo-SchumoschiferusL. The synthesized racemate is white needle crystal, insoluble in water, soluble in ethanol. In 1906, Walavm found about 2% in natural musk. In 1926 Ruzicka determined the structure as 3-methylcyclopentadecanone. The preparation method is to use the dodecatriene nickel complex to react with propadiene first to become a new complex with three carbon atoms added, and then react it with tertiary butyl isonitrile to generate fifteen members. The cyclic imine is then reduced by hydrolysis to obtain racemic musk ketone with a yield of 40%.
Musk ketone has the effect of fragrant opening, clearing meridians, reducing swelling and relieving pain. Small doses have excitatory effects on the central nervous system, while large doses have inhibitory effects. It has excitatory effect on isolated frog heart, and has male hormone-like effect and anti-inflammatory effect. Clinically used for coronary heart disease angina pectoris, vascular headache, sciatica, vitiligo, etc. This product has been synthetically produced in China. The pharmacological effects of synthetic products are similar to those of natural musk ketones.
White or colorless and dull crystals, colorless viscous liquid after melting; with sweet and soft musk aroma, extremely durable and powerful; melting point 33℃, boiling point 130℃/66.6Pa, 115～119℃/40Pa, relatively Density d4170.9214; Refractive index nD171.4809; Optical rotation -3°～10.6° (the synthetic product is racemic); soluble in ethanol and oil, almost insoluble in water.

 Chemical properties

Colorless oily liquid. The boiling point is 90°C, 130°C (66.7Pa), the relative density is 0.9221 (17/4°C), and the refractive index is 1.4802 (17°C). 

Use

●  Musk ketone is a representative variety of macrocyclic musk. The basic chemical structure of macrocyclic musk is 13-19 acyclic and contains at least one functional group. According to the chemical structure, it can be divided into cyclic esters, cyclic lactones, and cyclic oxygen-containing ketones. , cyclic ketolides, etc. Among the musk-type synthetic fragrances, the output of macrocyclic musk accounts for 5%. Musk ketone has a sweet and rich fragrance, which can be well blended with various spices. The aroma threshold is very low (0.001ppm-0.01ppm), and the fragrance lasts for a long time. It is an extremely effective fixative. Pharmacologically, it has the functions of invigorating the central nervous system, respiratory center and heart, and promoting the secretion of various urea bodies in drought disasters. It is an important drug for the treatment of confusion. It can protect the coronary arteries, increase coronary flow, and play a role in promoting blood circulation, reducing swelling and relieving pain. In addition, it has the effect of exciting the uterus and enhancing the contraction of uterine smooth muscle, so pregnant women should not use it. Musk is known for its ability to clear orifices, open meridians, penetrate muscles and bones, treat stroke, middle qi, middle evil and children's convulsions internally, and treat iron injury and sore externally. The addition of musk to advanced painting and calligraphy is not only elegant and fragrant, but also has the special effect of making the painting and calligraphy durable for a long time.

●  Used in medicines, musk fragrances, fixatives, etc.

Production method

●  There are many synthetic methods for musk ketone, and the raw materials can be selected from cyclohexanone, butadiene, cyclopentadecanone, etc. The method using butadiene as raw material is one of the most researched and promising methods at present. It is produced by three extractions of butadiene into dodeca-1,5,9-triene, and then hydrogenated and oxidized to form dodeca-1,5,9-triene. Cyclododecanone, and then through multi-step reaction to obtain musk ketone, the yield can reach 40%. Musk ketone is the main fragrance component of natural musk, generally containing 1.2%-1.4% of musk ketone. The natural musk is obtained by steam distillation for several days, extracting and distilling the infusion with ether, and making semicarbazide, then refining, decomposing, and finally refining by distillation.