3033-23-6

Usage

Uses

Used in Fragrance Industry:
(-)-Rose oxide is used as a fragrance ingredient in perfumes, soaps, and other personal care products for its unique and appealing floral scent, enhancing the overall aroma of these products.
Used in Food and Beverage Industry:
(-)-Rose oxide is used as a flavoring agent in the food and beverage industry, where it can add a pleasant and floral taste to various products.
Used in Therapeutic Applications:
(-)-Rose oxide is studied for its potential therapeutic properties, such as acting as an anti-inflammatory and an antioxidant, which could contribute to the development of new treatments and health products.

InChI:InChI=1/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10-/m1/s1

Upstream product

• 76936-31-7 (-)-(S)-Nerol oxide 
• 16122-01-3 3,7-Dimethyl-6-octene-1,5-diol 
• 124727-45-3 4-Bromo-4-methyl-2-(2-methyl-propenyl)-tetrahydro-pyran 
• 96154-45-9 3,7-dimethylocta-4,6-dien-1-ol 
• 88609-81-8 Dithiocarbonic acid S-methyl ester S-[(E)-2-methyl-3-((2R,4R)-4-methyl-tetrahydro-pyran-2-yl)-allyl] ester 
• 79981-82-1 (2S,4R)-2-(2-hydroxy-2-methylpropyl)-4-methyltetrahydropyran 
• 88609-80-7 Lithium; 2-methyl-1-((2R,4R)-4-methyl-tetrahydro-pyran-2-yl)-prop-2-en-1-olate 
• 88609-92-1 C₆H₁₁LiO 
• 906716-81-2 4-methyl-2-(thiophenyl)tetrahydropyran 
• 81925-86-2 3,7-dimethyl-5-(2'-methyl-2'-propenyl)-7-octen-1,5-diol 
• 81925-87-3 8-hydroxy-2,6-dimethyl-2-octen-4-one 
• 1121-84-2 4-methyl-tetrahydro-pyran-2-one 
• 73374-55-7 methyl (3R)-6-hydroxy-3,7-dimethyl-7-octenoate 
• 79664-97-4 methyl (3R)-3,7-dimethyl-6-oxo-7-octenoate 

Relevant academic research and scientific papers

Synthesis and odor of optically active rose oxide

Stereoselective synthesis of optically active rose oxide (1) by KHSO4 and Pd-BINAP-catalyzed cyclization of (3R)- and (3S)-3,7-dimethyl-6,7-octadien-1-ol (5) is described. One-pot synthesis of the (3R)- and (3S)-allenyl alcohol 5 from (3R)- and (3S)-citronellol (2) (98% ee) is also described. Furthermore, the odor properties of the four diastereomers of 1 are reported.

A method for preparing cis- rose ether (by machine translation)

The invention discloses a preparation method of cis-rose oxide. The preparation method comprises the following steps: performing epoxidation, epoxy rearrangement and selective oxidation on citronellol serving as a starting material, and preparing allene by using a benzenesulfonohydrazine intermediate; and cyclizing the allene under an acid condition to obtain the cis-rose oxide. By adopting the preparation method, the defects of low yield, use of various toxic reagents and metal reagents, difficulty in operating in a reaction process and the like in the conventional synthesis route are overcome, meanwhile the reaction stereoselectivity is improved, and synthesis of the cis-rose oxide can be realized. In particular, the using amount of aluminum isopropoxide is reduced; acetone, p-benzoquinone and the like are taken as oxidants, so that the production cost can be lowered effectively, greater convenience is brought to application, and industrial large-scale production is facilitated; and meanwhile reactions in a plurality of steps are performed in the same reaction kettle in a one-pot reaction way, so that the reaction process is simplified greatly, the production cost is lowered, and industrial production is facilitated.

Aluminium triflate catalysed cyclisation of unsaturated alcohols: novel synthesis of rose oxide and analogues

Aluminium trifluoromethanesulfonate was used as an efficient catalyst for the cycloisomerisation of several unsaturated alcohols into cyclic ethers such as rose oxide and some of its ether analogues.

Structure elucidation, enantioselective analysis, and biogenesis of nerol oxide in Pelargonium species

A novel enantioselective synthesis of nerol oxide (3,6-dihydro-4-methyl- 2-(2-methyl-1-propenyl)2H-pyran) was used for the determination of the absolute configuration at C-2. The order of elution of the enantiomers on octakis-(2,3-di-O-butyryl-6-O-tert-butyldimethylsilyl)-γ-cyclodextrin in OV 1701-vi as the chiral stationary phase in enantioselective GC was determined as (2R) before (2S). Enantioselective multidimensional GC/MS (enantio- MDGC/MS) was used for the determination of the enantiomeric ratios of nerol oxide in different geranium oils. As a result, in all investigated oils nerol oxide occurs as a racemate. The biogenesis of nerol oxide in Pelargonium species was investigated by feeding experiments using deuterium-labeled neryl glucoside as the precursor. The Pelargonium plants were able to convert the fed precursor into racemic nerol oxide, which has to be considered as a 'natural racemate'.

Process for producing a rose oxide

An improved process for production of an isomer mixture of Z- and E-2-?2-Methyl-prop-1-en-1-yl-!-4-methyl-tetrahydropyran, more commonly known under the name cis- and trans-rose oxide, which as a rule contains at least 80% of the natural Z-isomers (cis-rose oxide) which are valuable in the perfume industry.

Convenient Synthesis of Disubstituted Cyclic Ethers. Syntheses of (-)-cis-Rose Oxide and (cis-6-Methyltetrahydropyran-2-yl)acetic Acid

Disubstituted cyclic ethers are stereoselectively prepared on the successive treatment of δ- or ε-lactones with t-butyldimethylsiloxy-1-ethoxyethene and silyl nucleophiles in the presence of a catalytic amount of trityl hexachloroantimonate or a catalyst system of antimony pentachloride, chlorotrimethylsilane and tin(II) iodide.The present procedure is effectively applied to short syntheses of (-)-cis-rose oxide and (cis-6-methyltetrahydropyran-2-yl)acetic acid, a constituent of civet.

SYNTHESES OF TETRAHYDROPYRANS BY PPh3/CBr4 INDUCED CYCLIZATION OF ACETALS : APPLICATION TO A SYNTESIS OF ROSE OXIDE

Substituted tetrahydropyrans are prepared in good yields by PPh3/CBr4 induced cyclization of acetals.The utility of this new procedure is illustrated by the synthesis of cis-2-(methyl-1 propenyl)-4 methyltetrahydropyran (rose oxide).

173. β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Preparation of 3-Hydroxypropyl and 4-Hydroxybutyl Propenyl Ketones from γ- and δ-Lactones. Synthesis of (+/-)-Rose Oxide

Starting from γ- and δ-lactones 1-3, a two-step preparation of 3-hydroxypropyl and 4-hydroxybutyl propenyl ketones 10-18 is described, involving as the key step the β-cleavage of the bis(homoallylic) potassium alkoxides 4a-9a.This novel methodology is illustrated by a short synthesis of (+/-)-rose oxide (20).

Electrooxidative Cleavage of Carbon-Carbon Linkages. 1. Preparation of Acylic Oxoalkanoates from 2-Hydroxy- and 2-Acetoxy-1-cycloalkanones and Cycloalkanone Enol Acetates

A methodology is described for the synthesis of acyclic oxoalkanoates 2 by electrooxidative cleavage of carbon-carbon linkages of 2-oxocycloalkan-1-ols 1 and cycloalkanone enol acetates 3.The electrolysis of 1 was carried out in a MeOH-LiClO4-(Pt) system at a constant applied voltage of 20 V by using a divided cell, giving 2 in 82-97 percent yields.On the other hand, 3 was electrolyzed in MeOH-AcOH (10:1)-LiClO4-(Pt) at 2-8 deg to give 2 in 72-79 percent yields.Electrolysis of 4-hydroxy-p-menth-8-ene afforded methyl (3R)-3,7-dimethyl-6-oxo-7-octenoate, a chiral synthetic block for the synthesis of (+)-rose oxide, in 84 percent yield.Similarly, the procedure could be applied to the preparation of methyl(+)-6-oxo-6,7-dihydrocitronellate from (+)-menthone enol acetate (74 percent) as well as 4-hydroxy-p-menthone (94 percent).Other lithium salts, i.e., LiBF4 and CF3CO2Li, can be used for the present purpose, but there are some difficulties in producing 2 with Et4NOTs and Et4NClO4.A plausible mechanism of the formation of 2 from 1 is also discussed.