5258-11-7

Basic information

• Product Name: (-)-TRANS-ROSE OXIDE
• Synonyms: (-)-TRANS-ROSE OXIDE;(E)-roseoxide,(2R,4R)-tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran,(-)-trans-roseoxide,trans-roseoxide;(2R,4R)-2-(2-Methyl-1-propenyl)-4-methyltetrahydropyran;(-)-Dehydrolavender pyran;(2R,4R)-2-(2-Methyl-1-propenyl)-4-methyltetrahydro-2H-pyran;[2R,4R,(-)]-4-Methyl-2-(2-methyl-1-propenyl)tetrahydro-2H-pyran;(2R,4R)-Tetrahydro-4-methyl-2-(2-methylprop-1-enyl)-2H-pyran;(2R,4R)-rose oxide
• CAS NO: 5258-11-7
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.251
• Mol File: 5258-11-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 75-76 °C/12 mmHg(lit.)
• Flash Point: 68 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (-)-TRANS-ROSE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-TRANS-ROSE OXIDE(5258-11-7)
• EPA Substance Registry System: (-)-TRANS-ROSE OXIDE(5258-11-7)

Safety Data

• Safety Statements: 23-24/25
• Hazardous Substances Data: 5258-11-7(Hazardous Substances Data)

Usage

General Description

(-)-trans-Rose oxide is a naturally occurring organic compound found in various essential oils, notably rose and carnation. It is a cyclic ether with a distinctive floral aroma, often described as fresh, green, and somewhat woody. The compound has been widely used in the fragrance industry to impart a natural and delicate rose-like scent to perfumes, cosmetics, and household products. In addition to its aromatic properties, (-)-trans-rose oxide also exhibits insect-repellent and antimicrobial activities, which make it a useful ingredient in pest control products and air fresheners. Its pleasant scent and functional properties make (-)-trans-rose oxide a valuable and versatile chemical in the fragrance and flavor industries.

Upstream product

• 96154-45-9 3,7-dimethylocta-4,6-dien-1-ol 
• 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 
• 16122-01-3 3,7-Dimethyl-6-octene-1,5-diol 
• 79731-38-7 (3R,5E)-3,7-dimethylocta-5,7-dien-1-ol 
• 124727-45-3 4-Bromo-4-methyl-2-(2-methyl-propenyl)-tetrahydro-pyran 
• 76936-34-0 (+)-(R)-4-methylidene-2,2'-methylprop-1'-enyl-tetrahydropyran 
• 189211-35-6 (3S)-3,7-dimethyl-5,6-octadien-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 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 124727-44-2 4-Methoxymethoxy-2,6-dimethyl-hepta-1,5-diene 
• 88609-80-7 Lithium; 2-methyl-1-((2R,4R)-4-methyl-tetrahydro-pyran-2-yl)-prop-2-en-1-olate 
• 88609-92-1 C₆H₁₁LiO 

Relevant articles and documents

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.

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.

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).