5-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-4-penten-3-one
Basic information
- CAS
127-42-4- Standard SMILES
CCC(=O)C=CC1C(C)=CCCC1(C)C- InChIKey
VPKMGDRERYMTJX-UHFFFAOYSA-N- Molecular formula
- C14H22O
- Average molar mass
- 206.32 g/mol
- Monoisotopic mass
- 206.16706532
Overview
1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one is a clear, colorless to yellow liquid with a woody, violet odor. (NTP, 1992)
Names & identifiers
- Preferred name
- 5-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-4-penten-3-one
- IUPAC
- 1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-3-one
- English name
- FEMA 2597
- Molecular formula
- C14H22O
- Molecular weight
- 206.32
Names & synonyms
7779-30-8DTXSID60262401-(2,6,6-Trimethyl-2-cyclohexen-1-yl)pent-1-en-3-one5-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-4-penten-3-oneDTXCID206240RefChem:913092231-926-51-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-oneMethyl-alpha-iononeMETHYL IONANE GAMMA1-METHYL-ALPHA-IONONE5-(2,6,6-trimethylcyclohex-2-en-1-yl)-pent-4-en-3-one
Show more names
IRONE ALPHAALPHA-METHYL IONONEFEMA 2711METHYL IONONE ALPHAIRONALMethyl-α-iononeFEMA 2597METHYLIRIDONL-MethyliononeALPHA-CENTRONE
Methylionone (mixture of a- and b-, predominantly a-n-isomer)1-Penten-3-one, 1-[(1R)-2,6,6-trimethyl-2-cyclohexen-1-yl]-, (1E)-127-42-4SCHEMBL115151CHEMBL4569846AKOS024332472NS00079526
Database identifiers
- CAS
127-42-4、7779-30-8
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 294
Experimental & physicochemical properties
Fragrances
Fragrance Ingredient (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)pent-1-en-3-one) -> IFRA transparency List
Fragrance Ingredient (Methyl-alpha-ionone) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
0.93 at 77 °F (NTP, 1992) - Less dense than water; will float
0.921-0.930
Flavoring AgentsEU Flavoring substances
Solubility
less than 1 mg/mL at 68 °F (NTP, 1992)
(in ethanol)
Flash Pointgreater than 200 °F (NTP, 1992)
Boiling Point
291 °F at 16 mmHg (NTP, 1992)
238 °C
Vapor Densitygreater than 1 (NTP, 1992) (Relative to Air)
Refractive Index1.498-1.503
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
H411 (> 99.9%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1496 reports by companies from 10 notifications to the ECHA C&L Inventory.
This chemical does not meet GHS hazard criteria for 13.1% (38 of 289) of reports.
Warning
H315 (40.1%): Causes skin irritation [Warning Skin corrosion/irritation]
Hazard information
Regulatory Information
Chemical: 1-Penten-3-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, [R-(E)]-
Chemical: 1-Penten-3-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
1-Penten-3-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Penten-3-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)- 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)
[R-(E)]-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)pent-1-en-3-one: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
1-(2,6,6-trimethyl-2-cyclohexen-1-yl)pent-1-en-3-one: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety Information
IMAP assessments - Ionones: Human health tier II assessment
IMAP assessments - Ionones: Human health tier II assessment
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Chemistry & industry
Uses & manufacturing
U.S. Production2023: 1,000,000 - <2,500,000 lb
Consumer UsesFragrance
Industry UsesFragrance
Household Products
Information on 28 consumer products that contain Alpha-Methyl-Alpha-Ionone in the following categories is provided:
Information on 26 consumer products that contain 1-Trimethyl-2-Cyclohexenyl-1-Penten-3-One in the following categories is provided:
Use Classification
Fragrance Ingredients
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
1-Penten-3-one, 1-[(1R)-2,6,6-trimethyl-2-cyclohexen-1-yl]-, (1E)-: ACTIVE
1-Penten-3-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-: ACTIVE
Applications
DescriptionMethyl-α-ionone has an odor similar to α-ionone but lighter and more rounded with a pleasant, fruity, and sweet nuance. May be prepared by condensation of citral with methyl ethyl ketone (see methyl y-ionone or α-iso-methylionone).Pectic enzymes are indispensable for making high-density fruit juice concentrates or purees. Enzyme depectinization is required for apple juice concentrate of about 72° Brix, which is made on a large scale, as otherwise a gel would result rather than the desired liquid concentrate. Pectic enzymes are useful in treating orange, grape and prune pulps prior to vacuum puff drying.
Preparation methods
By condensation of citral with methyl ethyl ketone (see methyl γ-ionone or α-iso-methylionone)
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Related reactions
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Compound notes
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