Basic information
- CAS
80-71-7- Standard SMILES
CC1=C(O)C(=O)CC1- InChIKey
CFAKWWQIUFSQFU-UHFFFAOYSA-N- Molecular formula
- C6H8O2
- Average molar mass
- 112.13 g/mol
- Monoisotopic mass
- 112.0524295
Overview
Cyclotene is a metabolite found in or produced by Saccharomyces cerevisiae.
Names & identifiers
- Preferred name
- 2-Hydroxy-3-methyl-2-cyclopenten-1-one
- IUPAC
- 2-hydroxy-3-methylcyclopent-2-en-1-one
- English name
- Methyl cyclopentenolone
- Molecular formula
- C6H8O2
- Molecular weight
- 112.13
Names & synonyms
Show more names
Database identifiers
- CAS
80-71-7- PubChem CID
- 6660
- DTXSID
DTXSID4035128- UNII
- 627E92X64B
- EC Number
- 201-303-2
- Nikkaji
- J10.510D
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 156
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 104 · 104-108°C
- Boiling point
- 170.05 °C · 170.05°C (rough estimate)
- Density
- 1.0795 · 1.0795 (rough estimate)
- vapor pressure
- 2.1 hPa · 2.1hPa at 20℃
- FEMA
- 2700 · 2700 | METHYLCYCLOPENTENOLONE
- refractive index
- 1.4532 · 1.4532 (estimate)
- FLAVIS Number
- 7.056 · 07.056 | 3-Methylcyclopentan-1,2-dione
- Flash point
- 100 °C · 100°C
- storage temp.
- 2 °C · Store at +2°C to +8°C.
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 9.21 · 9.21±0.20(Predicted)
- form
- crystals
- color
- White crystalline powder or fine crystals
- Odor
- 1 % · at 1.00 % in dipropylene glycol. caramel maple syrup
- Odor Type
- caramellic
- biological source
- synthetic
- JECFA Number
- 418 · 418
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3
- InChIKey
- CFAKWWQIUFSQFU-UHFFFAOYSA-N
- SMILES
- CC1CCC(=O)C1=O
- LogP
- 0.4 at · 0.4 at 25℃
- CAS DataBase Reference
- 80 · 80-71-7(CAS DataBase Reference)
- FDA UNII
- 627 E92X64B · 627E92X64B
- NIST Chemistry Reference
- 2 · 2-Cyclopenten-1-one, 2-hydroxy-3-methyl-(80-71-7)
- EPA Substance Registry System
- Maple lactone (80-71-7)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H317-H318
- Precautionary statements
- 261 · P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-43
- Safety Statements
- 26 · 26-36/37-24/25-22
- WGK Germany
- 3 · 3
- RTECS
- 7298000 · GY7298000
- TSCA
- TSCA listed
- HS Code
- 29144090 · 29144090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Sens. 1
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Not Classified
Aggregated GHS information provided per 1763 reports by companies from 8 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 2-Cyclopenten-1-one, 2-hydroxy-3-methyl-
Regulation (EC) No 1831/2003 (amended)
2-Cyclopenten-1-one, 2-hydroxy-3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Cyclopenten-1-one, 2-hydroxy-3-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: 2-hydroxy-3-methylcyclopent-2-enone (EC: 201-303-2)
Cylcotene: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GY7298000
- hs_code
- 29144090
- risk_code
- 36/37/38-43
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xi
- safety_code
- 26-36/37-24/25-22
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H317-H318
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Sens. 1
- Precautionary statements
- P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
2-Cyclopenten-1-one, 2-hydroxy-3-methyl-: ACTIVE
Applications
OccurrenceReported to be found during the dry distillation of wood and in the corresponding tar oil. It has also been identified in fenugreek (FenaroWs Handbook of Flavor Ingredients, 1975).
UsesMethyl Cyclopentenolone is a flavoring agent that is a white crys- talline powder. it has a nutty odor suggesting a maple-licorice aroma when diluted. it is soluble in alcohol and propylene glycol, slightly soluble in most fixed oils, and sparingly soluble in water. it is obtained by synthesis. it is also termed 3-methyl-cyclopentane-1,2-dione.
UsesMethyl cyclopentenolone may be used as an analytical reference standard for the quantification of the analyte in commercial products using different chromatography techniques.
General DescriptionMethyl cyclopentenolone is one of the flavor compounds of maple syrup, coffee oil and wood smoke. It is reported to be one the key aroma compounds in Wasanbon sugar, contributing to the maple-like flavor. Methyl cyclopentenolone is also one of the major volatile compound formed during the thermal degradation of glucose.
Preparation methods
PreparationBy ketonic hydrolysis of the corresponding dicarboxylic ester (Arctander, 1969)
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
No reaction records under the current filter.
Compound notes
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