Methyl cyclopentenolone

Methyl cyclopentenolone occurs in beechwood tar and has a caramel-like (burnt sugar) odor. It has been identified as a flavor component in food. Crystals of the compound usually contain 1 mol of water. Synthetic routes of production are of limited importance in comparison with isolation from beechwood tar. Homologs of cyclotene such as 3-ethyl-2-hydroxy-2-cyclopenten-1-one, C
7
H
10
O
2
, Mr 126.16, 2-hydroxy-3,4-dimethyl-2-cyclopenten-1-one, C
7
H
10
O

DryPowder|white, crystalline powder with a nutty odour, maple-liquorice aroma in dilute solution

The IUPAC name of?2-Hydroxy-3-methyl-2-cyclopenten-1-one is?2-hydroxy-3-methylcyclopent-2-en-1-one. With the?CAS registry number 80-71-7,?it is also named?as?Cyclotene.?The product's category is?Clcohol Flavor.?It is?white crystalline powder?which is easily soluble in boiling water, soluble in ethanol, acetone and propylene glycol, and slightly soluble in most non-volatile oil.?Besides, this chemical can be obtained by?methyl furan and?dimethylamine. When heated to decomposition it emits acrid smoke and fumes.

The other characteristics of 2-Hydroxy-3-methyl-2-cyclopenten-1-one can be summarized as:?(1)ACD/LogP: 0.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.3; (4)ACD/LogD (pH 7.4): 0.29; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 34.75; (8)ACD/KOC (pH 7.4): 34.22; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.548; (13)Molar Refractivity: 29.08 cm³; (14)Molar Volume: 91.4 cm³; (15)Polarizability: 11.52×10^-24 cm³; (16)Surface Tension: 49.8 dyne/cm; (17)Enthalpy of Vaporization: 56.04 kJ/mol; (18)Vapour Pressure: 0.00484 mmHg at 25°C; (19)Tautomer Count: 16; (20)Exact Mass: 112.05243; (21)MonoIsotopic Mass: 112.05243; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 8; (24)Complexity: 156.

Uses of 2-Hydroxy-3-methyl-2-cyclopenten-1-one:?It is used?as?synergist of?flavor and sweetness. It is?mainly used for the preparation of?essence such as maple,?fumigation,?cream hard candy and?apricot. In addition, this chemical can react with?chloro-trimethyl-silane to get?1-methyl-2,3-bis(trimethylsilyloxy)-1,3-cyclopentadiene.?This reaction needs reagent?triethylamine, LiBr and solvent?tetrahydrofuran. The yield is 93%.?

People can use the following data to convert to the molecule structure.
1. SMILES:O=C1C(/O)=C(/C)CC1
2.?InChI:InChI=1/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3?
3.?InChIKey:CFAKWWQIUFSQFU-UHFFFAOYAU

The following are the toxicity data which has been tested.

The IUPAC name of?2-Hydroxy-3-methyl-2-cyclopenten-1-one is?2-hydroxy-3-methylcyclopent-2-en-1-one. With the?CAS registry number 80-71-7,?it is also named?as?Cyclotene.?The product's category is?Clcohol Flavor.?It is?white crystalline powder?which is easily soluble in boiling water, soluble in ethanol, acetone and propylene glycol, and slightly soluble in most non-volatile oil.?Besides, this chemical can be obtained by?methyl furan and?dimethylamine. When heated to decomposition it emits acrid smoke and fumes.

The other characteristics of 2-Hydroxy-3-methyl-2-cyclopenten-1-one can be summarized as:?(1)ACD/LogP: 0.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.3; (4)ACD/LogD (pH 7.4): 0.29; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 34.75; (8)ACD/KOC (pH 7.4): 34.22; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.548; (13)Molar Refractivity: 29.08 cm³; (14)Molar Volume: 91.4 cm³; (15)Polarizability: 11.52×10^-24 cm³; (16)Surface Tension: 49.8 dyne/cm; (17)Enthalpy of Vaporization: 56.04 kJ/mol; (18)Vapour Pressure: 0.00484 mmHg at 25°C; (19)Tautomer Count: 16; (20)Exact Mass: 112.05243; (21)MonoIsotopic Mass: 112.05243; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 8; (24)Complexity: 156.

Uses of 2-Hydroxy-3-methyl-2-cyclopenten-1-one:?It is used?as?synergist of?flavor and sweetness. It is?mainly used for the preparation of?essence such as maple,?fumigation,?cream hard candy and?apricot. In addition, this chemical can react with?chloro-trimethyl-silane to get?1-methyl-2,3-bis(trimethylsilyloxy)-1,3-cyclopentadiene.?This reaction needs reagent?triethylamine, LiBr and solvent?tetrahydrofuran. The yield is 93%.?

People can use the following data to convert to the molecule structure.
1. SMILES:O=C1C(/O)=C(/C)CC1
2.?InChI:InChI=1/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3?
3.?InChIKey:CFAKWWQIUFSQFU-UHFFFAOYAU

The following are the toxicity data which has been tested.

CHEMICAL IDENTIFICATION

RTECS NUMBER :

GY7298000

CHEMICAL NAME :

2-Cyclopenten-1-one, 2-hydroxy-3-methyl-

CAS REGISTRY NUMBER :

80-71-7

LAST UPDATED :

199701

DATA ITEMS CITED :

5

MOLECULAR FORMULA :

C6-H8-O2

MOLECULAR WEIGHT :

112.14

WISWESSER LINE NOTATION :

L5V BUTJ BQ C1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :

LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :

Intraperitoneal

SPECIES OBSERVED :

Rodent - rat

DOSE/DURATION :

500 mg/kg

TOXIC EFFECTS :

Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :

LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :

Intraperitoneal

SPECIES OBSERVED :

Rodent - mouse

DOSE/DURATION :

500 mg/kg

TOXIC EFFECTS :

Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :

LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :

Oral

SPECIES OBSERVED :

Rodent - guinea pig

DOSE/DURATION :

1400 mg/kg

TOXIC EFFECTS :

Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :

Sister chromatid exchange

TEST SYSTEM :

Human Lymphocyte

DOSE/DURATION :

1500 umol/L

REFERENCE :

MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 169,129,1986