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

6,10-Dimethyl-5,9-undecadien-2-one Basic information
Product Name:6,10-Dimethyl-5,9-undecadien-2-one
Synonyms:9-Undecadien-2-one,6,10-dimethyl-5;alpha,beta-Dihydropseudoionone;TRANS-6,10-DIMETHYL-5,9-UNDECADIEN-2-ONE;GERANYLACETONE(MIXTUREOFISOMERS);GERANYL-2-PROPANONE;FEMA 3542;CBI-BB ZERO/001230;6,10-DIMETHYL-5,9-UNDECADIEN-2-ONE
CAS:689-67-8
MF:C13H22O
MW:194.31
EINECS:211-711-2
Product Categories:Acyclic Monoterpenes;Biochemistry;Terpenes
Mol File:689-67-8.mol
6,10-Dimethyl-5,9-undecadien-2-one Structure
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.)
FEMA 3542 | 6,10-DIMETHYL-5,9-UNDECADIEN-2-ONE
refractive index n20/D 1.467(lit.)
Fp >230 °F
storage temp. Amber Vial, Refrigerator, Under inert atmosphere
solubility Chloroform, Dichloromethane (Slightly)
form Oil
color Colourless
Odorat 100.00 %. fresh rose leaf floral green magnolia aldehydic fruity
Odor Typefloral
Water Solubility Not miscible or difficult to mix in water. Soluble in alcohol.
JECFA Number1122
BRN 1722277
Stability:Light Sensitive
LogP4.13
CAS DataBase Reference689-67-8(CAS DataBase Reference)
NIST Chemistry Reference5,9-Undecadien-2-one, 6,10-dimethyl-(689-67-8)
EPA Substance Registry System5,9-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 Information
ProviderLanguage
SigmaAldrich English
ALFA English
6,10-Dimethyl-5,9-undecadien-2-one Usage And Synthesis
Chemical PropertiesGeranylacetone 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 Properties6,10-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
OccurrenceReported 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
UsesIt 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.
DefinitionChEBI: 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.
PreparationBy reaction of linalool and ethyl acetoacetate with an alkaline catalyst and subsequent rearrangement and decarboxylation.
ApplicationGeranylacetone is an intermediate in nerolidol synthesis. It is used in perfumery in rose compositions, for example, in soap perfumes.
Aroma threshold valuesDetection: 60 ppb to 6.4 ppm
Taste threshold valuesTaste characteristics at 12 ppm: floral, fruity, fatty, green, pear, apple and banana nuances
General Description6,10-Dimethyl-5,9-undecadien-2-one is one of the key volatile flavor compounds of tomato and certain species of mushroom.
Safety ProfileA skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
16-Denyprasterone acetate 2,10-Dimethyl-2,9-undecadien-6-one 6,10-Dimethyl-6,9-undecadien-2-one 7-isopropyl-2,10-dimethyl-8,10-undecadien-4-one Geranylacetone Propanoic acid, 2-oxo-, reaction products with (E)-6,10-dimethyl-5,9-undecadien-2-one 6,10-Dimethyl-3,9-undecadien-2-one CIS-GERANYLACETONE,(Z)-6,10-Dimethyl-5,9-undecadien-2-one,(5Z)-6,10-Dimethyl-5,9-undecadien-2-one

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