105-86-2

Basic information

• Product Name: 2,6-Octadien-1-ol,3,7-dimethyl-, 1-formate, (2E)-
• Synonyms: 2,6-Octadien-1-ol,3,7-dimethyl-, formate, (2E)- (9CI);2,6-Octadien-1-ol, 3,7-dimethyl-, formate,(E)- (8CI);Geraniol formate (6CI);(E)-3,7-Dimethyl-2,6-octadien-1-ol formate;(E)-3,7-Dimethyl-2,6-octadienyl formate;NSC 21736;trans-2,6-Dimethyl-2,6-octadien-8-yl methanoate;trans-3,7-Dimethyl-2,6-octadien-1-yl formate
• CAS NO: 105-86-2
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.2594
• EINECS: 203-339-4
• Product Categories: Alphabetical Listings;Flavors and Fragrances;G-H;Acyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 105-86-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 256.5 °C at 760 mmHg
• Flash Point: 109.1 °C
• Appearance: /
• Density: 0.908 g/cm³
• Vapor Pressure: 0.0154mmHg at 25°C
• Refractive Index: 1.458
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Insoluble
• CAS DataBase Reference: 2,6-Octadien-1-ol,3,7-dimethyl-, 1-formate, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Octadien-1-ol,3,7-dimethyl-, 1-formate, (2E)-(105-86-2)
• EPA Substance Registry System: 2,6-Octadien-1-ol,3,7-dimethyl-, 1-formate, (2E)-(105-86-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• RTECS: RG5925700
• Hazardous Substances Data: 105-86-2(Hazardous Substances Data)

Usage

Description

2,6-Octadien-1-ol,3,7-dimethyl-, 1-formate, (2E)-, also known as Geranyl formate, is a formate ester of geraniol with a fresh, green, leafy, rose odor and a bitter taste. It is a colorless liquid that is insoluble in alcohol and ether, and it occurs in several essential oils. Geranyl formate is prepared by direct esterification of geraniol with formic acid and is combustible.

Uses

Used in Perfumes and Soaps:
2,6-Octadien-1-ol,3,7-dimethyl-, 1-formate, (2E)is used as a fragrance ingredient in the perfumery industry for its fresh, crisp, herbal, fruity rose odor. It acts as a modifier in rose, geranium, and neroli compositions, enhancing the overall scent profile.
Used in Flavoring:
Geranyl formate is used as a flavoring agent in the food and beverage industry, providing green, floral, citrus, waxy, fruity, apple, and apricot-like taste characteristics at 10 ppm.
Used in Synthetic Neroli Oil:
2,6-Octadien-1-ol,3,7-dimethyl-, 1-formate, (2E)is utilized in the production of synthetic neroli oil, a popular ingredient in the perfume industry, due to its pleasant and versatile aroma.
Used in Aromatherapy:
Geranyl formate has a detection threshold of 200 ppb, making it a valuable component in aromatherapy for its fresh and uplifting scent.
Used in the Production of Essential Oils:
Geranyl formate is found in various essential oils, such as geranium oil, Ledum palustre oil, citrus peel oils, hop oil, rabbiteye blueberry, white wine, black tea, and fermented tea, contributing to their unique aromas and flavors.

Preparation

Prepared by direct esterifcation of geraniol with formic acid.

Flammability and Explosibility

Notclassified

Safety Profile

Low toxicity by ingestion and skin contact. A human skin irritant and an experimental eye irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

InChI:InChI=1/C11H18O2/c1-10(2)5-4-6-11(3)7-8-13-9-12/h5,7,9H,4,6,8H2,1-3H3/b11-7-

Upstream product

• 64-18-6 formic acid 
• 106-24-1 Geraniol 
• 201230-82-2 carbon monoxide 
• 113388-44-6 (formyloxy)(acetoxy)phenylmethane 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 79164-18-4 [(E)-2-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-vinyl]-benzene 
• 2436-90-0 dihydromyrcene 

Relevant articles and documents

Potassium Carboxylates by Direct Carbonylation of Potassium Alkoxides

Reaction of the K+ alkoxide of linalool (1) in benzene with CO at 425-440 bar and 120-130 degC for 12-30 h gave the K+ salt of 2,6-dimethyl-2-vinyl-5-heptenoic acid (4a) in a ca. 25percent yield based on ca. 65percent converted alkoxide.Reaction of the + 18-crown-6> alkoxide of 1 with CO at 50-55 bar and 40 degC for 90-140 h gave a mixture containing mainly the + 18-c-6> salts of 4a (ca. 62percent) and of the homogeranic acids 3a and 6a (together ca. 27percent of the mixture) in a ca. 35percent combined yield based on 50-60percent converted alkoxide.The uncomplexed or complexed K+ alkoxide of (S)-1 gave, with ca. 85percent net retention, the K+ salt of (S)-4a.Reaction of the + 18-c-6> alkoxide of geraniol (2) with CO at 50 bar and 40 degC for 65-70 h gave myrcene (10) and geranyl formate (11) in a ca. 40-50percent yield each based on ca. 85percent converted alkoxide.Reaction of the + 18-c-6> alkoxide of 3-pentyl-1,4-pentadien-3-ol (14) at 50 bar and r.t. for 70 h gave a mixture of the + 18-c-6> salts of 2-pentyl-2-vinyl-3-butenoic acid (15a) (67percent) and the 4-pentyl-2,4-hexadienoic acids 18a and l9a (together 23percent of the mixture) in a ca. 90percent combined yield based on ca. 65percent converted alkoxide.

Efficient Enzymatic Preparation of Flavor Esters in Water

A straightforward biocatalytic method for the enzymatic preparation of different flavor esters starting from primary alcohols (e.g., isoamyl, n-hexyl, geranyl, cinnamyl, 2-phenethyl, and benzyl alcohols) and naturally available ethyl esters (e.g., formate, acetate, propionate, and butyrate) was developed. The biotransformations are catalyzed by an acyltransferase from Mycobacterium smegmatis (MsAcT) and proceeded with excellent yields (80-97%) and short reaction times (30-120 min), even when high substrate concentrations (up to 0.5 M) were used. This enzymatic strategy represents an efficient alternative to the application of lipases in organic solvents and a significant improvement compared with already known methods in terms of reduced use of organic solvents, paving the way to sustainable and efficient preparation of natural flavoring agents.

TiCl4/Et3N-Mediated Condensation of Acetate and Formate Esters: Direct Access to β-Alkoxy- and β-Aryloxyacrylates

A methodology to build (E)-β-alkoxy- and (E)-β-aryloxyacrylate moieties from acetate and formate esters promoted by the TiCl4/Et3N system is presented. The reaction is compatible with a broad range of structural skeletons and elapses through an unusual condensation pathway. Taking into account the obtained results, we propose a plausible mechanism involving a bimetallic titanium intermediate for this type of transformation.