6-Methyl-5-hepten-2-one

6-Methyl-5-hepten-2-one Basic information
Product Name:6-Methyl-5-hepten-2-one
Synonyms:2-Methyl-2-hepten-6-one (=6-Methyl-5-hepten-2-one);METHYL HEPTENONE, NATURAL;6-Methyl-5-henten-2-one;2-Methyl-6-oxo-2-heptene;2-methylhept-2-en-6-one;2-Oxo-6-methylhept-5-ene;5-Hepten-2-one,6-methyl-;6-methyI-5-hepten-2-one
CAS:110-93-0
MF:C8H14O
MW:126.2
EINECS:203-816-7
Product Categories:C7 to C8;Carbonyl Compounds;Alphabetical Listings;Certified Natural ProductsFlavors and Fragrances;Flavors and Fragrances;Ketones;M-N
Mol File:110-93-0.mol
6-Methyl-5-hepten-2-one Structure
6-Methyl-5-hepten-2-one Chemical Properties
Melting point -67.1 °C
Boiling point 73 °C18 mm Hg(lit.)
density 0.855 g/mL at 25 °C(lit.)
vapor pressure 1.121hPa at 20℃
FEMA 2707 | 6-METHYL-5-HEPTEN-2-ONE
refractive index n20/D 1.439(lit.)
Fp 123 °F
storage temp. Sealed in dry,2-8°C
solubility Soluble in methanol and chloroform.
form neat
color Colorless to Light yellow
Specific Gravity0.855
Odorat 10.00 % in dipropylene glycol. citrus green musty lemongrass apple
PH6.6 (3g/l, H2O, 25℃)
Odor Typecitrus
explosive limit1.1-7.3%(V)
Water Solubility insoluble
JECFA Number1120
BRN 1741705
LogP2.07 at 25℃
CAS DataBase Reference110-93-0(CAS DataBase Reference)
NIST Chemistry Reference5-Hepten-2-one, 6-methyl-(110-93-0)
EPA Substance Registry System6-Methyl-5-hepten-2-one (110-93-0)
Safety Information
Risk Statements 10-36/37/38
Safety Statements 16-24/25
RIDADR UN 1224 3/PG 3
WGK Germany 1
RTECS MJ9700000
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29141990
toxicityThe acute oral LD50 in rats was reported as 3.5 g/kg (B?r & Griepentrog, 1967) and as 4T g/kg (3.33-5.04 g/kg) (Keating, 1972). The acute dermal LD50 exceeded 5 g/kg (Keating, 1972).
MSDS Information
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Methylheptenone English
SigmaAldrich English
ACROS English
ALFA English
6-Methyl-5-hepten-2-one Usage And Synthesis
Description6-Methyl-5-hepten-2-one has a strong, fatty, green, citrus-like odor, and a bittersweet taste reminiscent of pear. May be prepared from oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2C 03, and subsequent distillation and vacuum fractionation; from acetoacetic ester and methylbuten-3-ol-2 with aluminum alcoholate in Carroll’s reaction followed by pyrolysis of the ester.
Chemical Properties6-Methyl-5-hepten-2-one has a strong, fatty, green, citrus-like odor and bittersweet taste reminiscent of pear.
Chemical PropertiesCLEAR SLIGHTLY YELLOW LIQUID
Chemical Properties6-Methyl-5-hepten-2-one is an important intermediate in the synthesis of terpenoids. Its odor properties are not impressive. It occurs in nature as a degradation product of terpenes. (Z)- and (E)-Tagetone, [3588-18-9], [6752-80-3], are major components of tagetes oil. Solanone [1937-54-8] and pseudoionone [141-10-6] are acyclicC13 ketoneswith a terpenoid skeleton. Solanone is one of the flavor-determining constituents of tobacco, and pseudoionone is an intermediate in the synthesis of ionones.
OccurrenceOriginally identified in lemongrass; it has been reported found in the essential oils of palmarosa, lemon, citronella, vervain, geranium, Ocimum canum, Artemisia scoparia, Urtica dioica and others. Also reported found in apple, apricot, sweet and sour cherry, orange juice, citrus peel oils, bilberry, lingonberry, cranberry, guava, grapes, melon, peach, pear, raspberry, strawberry, blackberry, carrot, celery, tomato, potato, clove bud and leaf, ginger, peppermint oil, thymus, Gruyere cheese, butter, beef, hop oil, beer, cognac, cider, white wine, cocoa, tea, peanut oil, avocado, Arctic bramble, cloudberry, olive, passion fruit, plumcot, rose apple, marjoram, starfruit, mango, fig, rice, rice bran, quince, origanum, calamus, buckwheat, corn oil, wort, dried bonito, elderberry, cherimoya, kiwifruit, mountain papaya, endive, lemon balm, clary sage, nectarine, clam, Cape gooseberry, maté, German chamomile oil and mastic gum leaf oil, lime oil and apple brandy
Uses6-Methyl-hepten-2-one is used in the synthesis of thyrsiferyl 23-Acetate which acts as an anti-leukemic inducer of apoptosis.
UsesOrganic synthesis, inexpensive perfumes, fla-voring.
DefinitionChEBI: A heptenone that is hept-5-en-2-one substituted by a methyl group at position 6. It is a volatile oil component of citronella oil, lemon-grass oil and palmarosa oil.
PreparationFrom oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2CO3, and subsequent distillation and vacuum fractionation; from acetoacetic ester and methyl-buten-3-ol-2 with aluminum alcoholate in Carroll’s reaction followed by pyrolysis of the ester
Aroma threshold valuesDetection: 50 ppb
Taste threshold valuesTaste characteristics at 10 ppm: green, vegetative, musty, apple, banana and green bean-like.
Synthesis Reference(s)Tetrahedron Letters, 28, p. 4893, 1987 DOI: 10.1016/S0040-4039(00)96654-1
Synthesis, p. 796, 1981 DOI: 10.1055/s-1981-29599
General Description6-Methyl-5-hepten-2-one is one of the main flavor volatile of tomatoes.
Flammability and ExplosibilityFlammable
Safety ProfileModerately toxic by ingestion. A skin irritant. Flammable liquid when exposed to heat, sparks, or flame. When heated to decomposition it emits acrid smoke and irritating fumes.
6-Methyl-5-hepten-2-one Preparation Products And Raw materials
Raw materialsIsoprene-->6-methyl-6-hepten-2-one-->6-METHYL-2-HEPTANONE
Preparation ProductsCitral-->Linalool-->GERANIC ACID-->6-AMINO-2-METHYL-2-HEPTANOL-->3,7-DIMETHYL-1-OCTEN-3-OL-->6-METHYL-2-HEPTANOL-->ETHYL GERANATE
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