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3-Methyl-1,2-cyclopentanedione

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CAS:765-70-8
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3-Methyl-1,2-cyclopentanedione Basic information
Application
Product Name:3-Methyl-1,2-cyclopentanedione
Synonyms:3-Methyl-1,2-cyclopentadione;3-Methylcyclopenta-1,2-dione;3-Methyl-1,2-cyclopentanedione,99%;3-Methyl-1,2-cyclopentanedione, 99% 10GR;3-Methyl-1,2-cyclopentanedione, 99% 50GR;Methylcyclopentane-1,2-;3-Methyl-1,2-cyclopentanedione 99%;2-Cyclopentanedione,3-methyl-1
CAS:765-70-8
MF:C6H8O2
MW:112.13
EINECS:212-154-8
Product Categories:Indolines ,Indoles ,Indazoles
Mol File:765-70-8.mol
3-Methyl-1,2-cyclopentanedione Structure
3-Methyl-1,2-cyclopentanedione Chemical Properties
Melting point 104-108 °C(lit.)
Boiling point 170.05°C (rough estimate)
density 1.0795 (rough estimate)
FEMA 2700 | METHYLCYCLOPENTENOLONE
refractive index 1.4550 (estimate)
Fp 100 °C
storage temp. Store below +30°C.
solubility soluble in Methanol
form Powder
color White to off-white
Odorat 10.00 % in dipropylene glycol. sweet caramel maple sugar coffee woody
Odor Typecaramellic
Water Solubility soluble
λmax259nm(EtOH)(lit.)
JECFA Number418
BRN 2076520
InChI1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h4H,2-3H2,1H3
InChIKeyOACYKCIZDVVNJL-UHFFFAOYSA-N
SMILESCC1CCC(=O)C1=O
LogP0.04
CAS DataBase Reference765-70-8(CAS DataBase Reference)
NIST Chemistry Reference1,2-Cyclopentanedione, 3-methyl-(765-70-8)
EPA Substance Registry System1,2-Cyclopentanedione, 3-methyl- (765-70-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38-43
Safety Statements 22-24/25-36/37-26-36
WGK Germany 3
TSCA TSCA listed
HS Code 29142900
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
2-Hydroxy-3-methyl-2-cyclopenten-1-one English
SigmaAldrich English
ACROS English
ALFA English
3-Methyl-1,2-cyclopentanedione Usage And Synthesis
Application3-Methylcyclopentane-1,2-dione, also known as methylcyclopentenolone, is an important food flavoring agent with a prominent sweet maple-like aroma, hence the name maple lactone. Due to its caramel-like sweet aroma and nutty aroma, it has a wide range of uses. It can be used in various flavorings such as coffee, cocoa, chocolate, and nuts, and is also widely used in tobacco flavorings, detergents, and cosmetics. It can also be directly applied to foods such as bread and pastries.
DescriptionMethylcyclopentenolone has a sweet flavor somewhat similar to licorice.
Chemical PropertiesMethylcyclopentenolone has a sweet flavor somewhat similar to licorice. This compound is also reported to have a nutty odor, and a maple-licorice aroma in dilute solution
Chemical PropertiesWHITE TO OFF-WHITE POWDER
OccurrenceReported formed during the dry distillation of wood; found also in the corresponding tar oil; identified in fenugreek. Also reported found in black currants, onion, wheat bread, cured and cooked pork, beer, cocoa, coffee, barley, filbert, almond, sukiyaki, licorice, dried bonito and roasted chicory root
PreparationSublimes and distills at atmospheric pressure with decomposition.
DefinitionChEBI: 3-Methyl-1,2-cyclopentanedione is a cyclic ketone.
Aroma threshold valuesDetection: 300 ppb
Taste threshold valuesTaste characteristics at 5 ppm: sweet, maple, bready, caramellic with nutty nuances.
Synthesis Reference(s)Synthesis, p. 104, 1975 DOI: 10.1055/s-1975-23673
General Description3-Methyl-1,2-cyclopentanedione is present in coffee and is capable of scavenging peroxynitrite. It also has anti-inflammatory effects.
Synthesis
1-Hydroxyhexane-2,5-dione

65313-46-4

3-Methyl-1,2-cyclopentanedione

765-70-8

1-Hydroxy-2,5-hexanedione (130 mg) was used as starting material and dissolved in water at 80 °C. Sodium bicarbonate (8.4 mg) was added as a catalyst and the reaction lasted for 12 hours. Upon completion of the reaction, extraction was carried out using chloroform to isolate the product. Purification by silica gel column chromatography afforded 3-methylcyclopentane-1,2-dione (91 mg) in 81% yield. The final product was analyzed by GC-MS and confirmed by comparison with 3-methylcyclopentane-1,2-dione standard.

References[1] Patent: CN108129278, 2018, A. Location in patent: Paragraph 0018-0025
3-Methyl-1,2-cyclopentanedione Preparation Products And Raw materials
Raw materials1-Hydroxyhexane-2,5-dione-->Sodium bicarbonate
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