6,10-Dimethyl-5,9-undecadien-2-one Chemical Properties

Boiling point:

254-258 °C(lit.)

Density 

0.873 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.467(lit.)

FEMA 

3542 | 6,10-DIMETHYL-5,9-UNDECADIEN-2-ONE

Flash point:

>230 °F

storage temp. 

Amber Vial, Refrigerator, Under inert atmosphere

solubility 

Chloroform, Dichloromethane (Slightly)

form 

Oil

color 

Colourless

Odor

at 100.00 %. fresh rose leaf floral green magnolia aldehydic fruity

Odor Type

floral

Water Solubility 

Not miscible or difficult to mix in water. Soluble in alcohol.

JECFA Number

1122

BRN 

1722277

Stability:

Light Sensitive

LogP

4.13

CAS DataBase Reference

689-67-8(CAS DataBase Reference)

NIST Chemistry Reference

5,9-Undecadien-2-one, 6,10-dimethyl-(689-67-8)

EPA Substance Registry System

5,9-Undecadien-2-one, 6,10-dimethyl- (689-67-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

RTECS 

YQ1190000

TSCA 

Yes

HS Code 

2914199090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6,10-Dimethyl-5,9-undecadien-2-one Usage And Synthesis

Chemical Properties

Geranylacetone occurs in (5Z)-trans as well as in (5E)-trans form and has been identified in fruits and in essential oils. It is a colorless liquid with a fresh, green, slightly penetrating, rose-like odor.
Geranylacetone is an intermediate in the synthesis of other fragrance substances. It is mainly produced from linalool. Another route starts from myrcene, to which methyl acetoacetate is added under rhodium catalysis; geranylacetone is subsequently obtained after saponification and decarboxylation. It is used in perfumery in rose compositions, for example, in soap perfumes.

Chemical Properties

6,10-Dimethyl-5,9-undecadien-2-one has a green and rosy floral odor and fresh-floral, light, but rather penetrating sweet-rosy, slightly green, magnolia-like odor. It blends well in lavender and fruity notes, where it imparts a clean and natural character. It helps to round out floral bouquets

Occurrence

Reported found in oil of citronella, yellow passion fruit, peppermint, Scotch spearmint oil, Japanese seafood, scallop, tomato, tomato paste, citrus peel oils, carrots, papaya, melon, Parmesan cheese, milk powder, cognac, tea, starfruit, figs, mango, red sage, nectarines, clams, pork, anise, and hyssop

Uses

It is used as a flavoring agent and adjuvant. It is also employed as a substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.

Preparation

By reaction of linalool and ethyl acetoacetate with an alkaline catalyst and subsequent rearrangement and decarboxylation.

Application

Geranylacetone is an intermediate in nerolidol synthesis. It is used in perfumery in rose compositions, for example, in soap perfumes.

Definition

ChEBI: Geranyl acetone is a monoterpene ketone in which an (E)-geranyl group is bonded to one of the alpha-methyls of acetone. It is a component of essential oils from various plants including Nelumbo nucifera. It has a role as a flavouring agent, a fragrance, a volatile oil component and a plant metabolite. It contains a geranyl group.

Aroma threshold values

Detection: 60 ppb to 6.4 ppm

Taste threshold values

Taste characteristics at 12 ppm: floral, fruity, fatty, green, pear, apple and banana nuances

General Description

6,10-Dimethyl-5,9-undecadien-2-one is one of the key volatile flavor compounds of tomato and certain species of mushroom.

Safety Profile

A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

6,10-Dimethyl-5,9-undecadien-2-one(689-67-8)Related Product Information

• 16-Denyprasterone acetate
• CIS-GERANYLACETONE,(Z)-6,10-Dimethyl-5,9-undecadien-2-one,(5Z)-6,10-Dimethyl-5,9-undecadien-2-one
• Geranylacetone
• 7-isopropyl-2,10-dimethyl-8,10-undecadien-4-one
• 6,10-Dimethyl-6,9-undecadien-2-one
• Propanoic acid, 2-oxo-, reaction products with (E)-6,10-dimethyl-5,9-undecadien-2-one
• 6,10-Dimethyl-3,9-undecadien-2-one
• 2,10-Dimethyl-2,9-undecadien-6-one