57784-11-9

Basic information

• Product Name: ()-2,6-dimethyloct-7-ene-2,6-diol
• Synonyms: 2,6-Dimethyloct-7-ene-2,6-diol; 249-511-2
• CAS NO: 57784-11-9
• Molecular Formula: C₁₀H₂₀O₂
• Molecular Weight: 172.2646
• EINECS: 260-961-9
• Mol File: 57784-11-9.mol

Chemical Properties

• Boiling Point: 283.9°C at 760 mmHg
• Flash Point: 129.4°C
• Density: 0.937g/cm³
• Vapor Pressure: 0.000356mmHg at 25°C
• Refractive Index: 1.468
• CAS DataBase Reference: ()-2,6-dimethyloct-7-ene-2,6-diol(CAS DataBase Reference)
• NIST Chemistry Reference: ()-2,6-dimethyloct-7-ene-2,6-diol(57784-11-9)
• EPA Substance Registry System: ()-2,6-dimethyloct-7-ene-2,6-diol(57784-11-9)

Safety Data

• Hazardous Substances Data: 57784-11-9(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
Geraniol is used as a fragrance ingredient in perfumes, soaps, and skincare products due to its sweet, floral aroma.
Used in Natural Insect Repellents:
Geraniol is used as an active ingredient in natural insect repellents, thanks to its antibacterial, antifungal, and antioxidant properties.
Used in Cosmetic Industry:
Geraniol is used in the cosmetic industry for its pleasant aroma and beneficial properties, making it a popular ingredient in various skincare and beauty products.
Used in Medical Applications:
Geraniol has potential therapeutic uses, such as anti-cancer and anti-inflammatory effects, and has been studied for its potential in treating neurological disorders.
Overall, geraniol is a versatile compound with a range of applications in the fragrance, cosmetic, and medical industries.

Upstream product

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Downstream Products

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Relevant articles and documents

Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic [2,3]-Meisenheimer Rearrangements

Chiral acyclic tertiary allylic alcohols are very important synthetic building blocks, but their enantioselective synthesis is often challenging. A major limitation in catalytic asymmetric 1,2-addition approaches to ketones is the enantioface differentiation by steric distinction of both ketone residues. Herein we report the development of a catalytic asymmetric Meisenheimer rearrangement to overcome this problem, as it proceeds in a stereospecific manner. This allows for high enantioselectivity also for the formation of products in which the residues at the generated tetrasubstituted stereocenter display a similar steric demand. Low catalyst loadings were found to be sufficient and the reaction conditions were mild enough to tolerate even highly reactive functional groups, such as an enolizable aldehyde, a primary tosylate, or an epoxide. Our investigations suggest an intramolecular rearrangement pathway.

IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

5, 9-dimethyl-9-hydroxy-decen-4-al, having the formula (I).

Biotransformation of (-)-dihydromyrcenyl acetate using the plant parasitic fungus Glomerella cingulata as a biocatalyst

The microbial transformation pf (-)-dihydromyrcenyl acetate was investigated using the plant parasitic fungus Glomerella cingulata. As a result, (-)-dihydromyrcenyl acetate was converted to dihydromyrcenol, 3,7-dihydroxy-3,7-dimethyl-1-octene-7-carboxylate, 3,7-dihydroxy-3,7-dimethyl-1-octene, 3,7-dimethyloctane-1,2,7-triol-7-carboxylate, and 3,7-dimethyloctane-1,2,7-triol. In addition, microbial transformation of dihydromyrcenol by G. cingulata was carried out. The metabolic pathway of (-)-dihydromyrcenyl acetate is discussed.

(S)-3,7-Dimethyl-5-octene-1,7-diol and Related Oxygenated Monoterpenoids from Petals of Rosa damascena Mill

The methanolic extract obtained from rose flowers was subjected to XAD-2 adsorption chromatography. Prefractionation of the methanolic eluate using multilayer coil countercurrent chromatography (MLCCC) yielded five subfractions. From the least polar subfraction V, a major amount of the key odorants of rose oil, that is, isomeric rose oxides 1a/b, was liberated upon heat treatment at pH 2.5. Further Chromatographic workup of fraction V led, for the first time, to the identification of the genuine rose oxide precursor (S)-3,7-dimethyl-5-octene-1,7-diol (2). In addition to diol 2, the following monoterpene diols have been identified: 3,7-dimethyl-7-octene-1,6-diol (3), 2,6-dimethyl-1,7-octadiene-3,6-diol (4), (2E,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol (5), (2E)-3,7-dimethyl-2,7-octadiene-1,6-diol (6), (2Z,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol (7), (2Z)-3,7-dimethyl-2,7-octadiene-1,6-diol (8), (Z)-2,6-dimethyl-2-octene-1,8-diol (9), (E)-2,6-dimethyl-2-octene-1,8-diol (10), (Z)-2,6-dimethyl-2,7-octadiene-1,6-diol (11), (E)-2,6-dimethyl-2,7-octadiene-1,6-diol (12), (2E,6E)-2,6-dimethyl-2,6-octadiene-1,8-diol (13), (2E,6Z)-2,6-dimethyl-2,6-octadiene-1,8-diol (14), 2,6-dimethyloctane-1,8-diol (15), 2,6-dimethyl-7-octene-1,6-diol (16), (E)-3,7-dimethyl-2-octene-1,8-diol (17), (Z)-3,7-dimethyl-2-octene-1,8-diol (18), 3,7-dimethyloctane-1,7-diol (19), 2,6-dimethyl-7-octene-2,6-diol (20), 3,7-dimethyl-6-octene-1,3-diol (21) and (2E)-3,7-dimethyl-2,6-octadiene-1,4-diol (22).

Micellar-Induced Selectivity and Rate Enhancement in the Acid-Catalyzed Cyclization and Rearrangement of Monoterpenes. The Solvolysis of Linalyl and Geranyl Acetates

The monoterpene linalyl acetate (1) undergoes acid-catalyzed solvolysis/cyclization at pH 3 in HCl/citrate buffer to yield three major acyclic alcohols, geranol (2), linalool (3), and nerol (4), and one cyclic alcohol, α-terpineol (5).The acyclic/cyclic alcohol ratio is 2.7 in no sodium dodecyl sulfate (SDS) controls after ca. 3 half-lives, compared to 8.5 when the reaction is carried out in a SDS micelle.No micellar rate effect was observed.The SDS-induced selectivity is explained in terms of the micelle-favoring acyclic conformers of linalyl acetate.In contrast to linalyl acetate, solvolysis of geranyl acetate (6) in the SDS micelle at pH 2 gives little product selectivity but yields a 7-fold rate effect relative to no SDS controls.This rate effect results in very different product distributions after 90percent completion of the reaction.The observed SDS rate effect for geranyl acetate is compatible with a difference in solvolysis mechanism for linalyl and geranyl acetate.

NEW LINALOOL DERIVATIVES IN MUSCAT OF ALEXANDRIA GRAPES AND WINES

The CHCl3 extract of Muscat of Alexandria grapes as well as extracts of wines made from these grapes were found to contain 3,7-dimethyloct-1-en-3,6,7-triol, 3,7-dimethyloct-1-en-3,7-diol, 3,7-dimethyloct-1,7-dien-3,6-diol and 3,7-dimethylocta-1,5-dien-3,7-diol. - Key Word Index: Vitis vinifera; Muscat of Alexandria; grapes; wine; acyclic monoterpenoids; 3,7-dimethyloct-1-en-3,6,7-triol; 3,7-dimethyloct-1-en-3,7-diol; 3,7-dimethylocta-1,7-dien-3,6-diol; 3,7-dimethylocta-1,5-dien-3,7-diol.