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)

refractive index 

1.4550 (estimate)

FEMA 

2700 | METHYLCYCLOPENTENOLONE

Flash point:

100 °C

storage temp. 

Store below +30°C.

solubility 

soluble in Methanol

form 

Powder

color 

White to off-white

Odor

at 10.00 % in dipropylene glycol. sweet caramel maple sugar coffee woody

Odor Type

caramellic

Water Solubility 

soluble

λmax

259nm(EtOH)(lit.)

JECFA Number

418

BRN 

2076520

LogP

0.04

CAS DataBase Reference

765-70-8(CAS DataBase Reference)

NIST Chemistry Reference

1,2-Cyclopentanedione, 3-methyl-(765-70-8)

EPA Substance Registry System

1,2-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 

Yes

HS Code 

29142900

MSDS

• Language:English Provider:2-Hydroxy-3-methyl-2-cyclopenten-1-one
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Methyl-1,2-cyclopentanedione Usage And Synthesis

Application

3-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.

Description

Methylcyclopentenolone has a sweet flavor somewhat similar to licorice.

Chemical Properties

Methylcyclopentenolone 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 Properties

WHITE TO OFF-WHITE POWDER

Occurrence

Reported 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

Preparation

Sublimes and distills at atmospheric pressure with decomposition.

Definition

ChEBI: 3-Methyl-1,2-cyclopentanedione is a cyclic ketone.

Aroma threshold values

Detection: 300 ppb

Taste threshold values

Taste 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 Description

3-Methyl-1,2-cyclopentanedione is present in coffee and is capable of scavenging peroxynitrite. It also has anti-inflammatory effects.

Synthesis

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

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