Basic information
- Standard SMILES
CC(=O)CCC=C(C)C- InChIKey
UHEPJGULSIKKTP-UHFFFAOYSA-N- Molecular formula
- C8H14O
- Average molar mass
- 126.2 g/mol
- Monoisotopic mass
- 126.10446507
Overview
Sulcatone is a heptenone that is hept-5-en-2-one substituted by a methyl group at position 6. It is a volatile oil component of citronella oil, lemon-grass oil and palmarosa oil. It has a role as a volatile oil component, an alarm pheromone and a plant metabolite. It is a heptenone and a methyl ketone.
Names & identifiers
- Preferred name
- 6-Methyl-5-hepten-2-one
- IUPAC
- 6-methylhept-5-en-2-one
- English name
- 6-Methyl-5-hepten-2-one
- Molecular formula
- C8H14O
- Molecular weight
- 126.2
Names & synonyms
6-METHYL-5-HEPTEN-2-ONE6-Methylhept-5-en-2-one110-93-0SulcatoneMETHYL HEPTENONE5-HEPTEN-2-ONE, 6-METHYL-2-Oxo-6-methylhept-5-eneFEMA No. 2707DTXSID5021629NSC-15294DTXCID501629CHEBI:16310
Show more names
FEMA 2707methyl-5-hepten-2-one5-Hepten-2-one,6-methyl-Methyl hepten6-methyl-5-hepten-2-on
RefChem:818618DTXSID9027152203-816-7Methylheptenone2-Methyl-2-hepten-6-one6-Methyl-5-heptene-2-oneprenylacetone6-Methyl-hepten-2-one
Database identifiers
- CAS
110-93-0、409-02-9- PubChem CID
- 9862
- DTXSID
DTXSID5021629- ChEMBL
CHEMBL46340- ChEBI
CHEBI:16310- UNII
- 448353S93V
- EC Number
- 203-816-7、206-990-2
- Nikkaji
- J58.156I
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 119
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Aliphatic Ketones, Other
Other Classes -> Aliphatic Ketones, Other
LipidsFatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SpringerMaterials PropertiesBoiling point
Fragrances
Fragrance Ingredient (6-Methyl-5-hepten-2-one) -> IFRA transparency List
Fragrance Ingredient (Methylheptenone (isomer unspecified)) -> IFRA transparency List
OdorPOWERFUL, FATTY, GREEN, CITRUS ODOR
TasteFRUITY TASTE
Food AdditivesFLAVOR ENHANCER -> FDA Substance added to food
Density
0.8546 @ 16 °C/4 °C
0.846-0.854
Flavoring AgentsEU Flavoring substances
Color/FormCOLORLESS LIQUID
Solubility
INSOL IN WATER; SOL IN ALL PROP WITH ALCOHOL, ETHER
3351 /mg/L @ 20 °C (exp)
Insoluble in water; soluble in oils and organic solvents
Miscible at room temperature (in ethanol)
Flash Point135 °F (57 °C)
Physicochemical properties
- Melting point
- -67.1 °C · -67.1 °C
- Boiling point
- 73 °C18 · 73 °C18 mm Hg(lit.)
- Density
- 0.855 g/mL · 0.855 g/mL at 25 °C(lit.)
- vapor pressure
- 1.121 hPa · 1.121hPa at 20℃
- FEMA
- 2707 · 2707 | 6-METHYL-5-HEPTEN-2-ONE
- refractive index
- 20 · n20/D 1.439(lit.)
- FLAVIS Number
- 7.015 · 07.015 | 6-Methylhept-5-en-2-one
- Flash point
- 123 °F · 123 °F
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Soluble in methanol and chloroform.
- form
- Liquid
- color
- Colorless to Light yellow
- Specific Gravity
- 0.855 · 0.855
- PH
- 6.6 · 6.6 (3g/l, H2O, 25℃)
- Odor
- 10 % · at 10.00 % in dipropylene glycol. citrus green musty lemongrass apple
- Odor Type
- citrus
- biological source
- synthetic
- explosive limit
- 1.1 · 1.1-7.3%(V)
- Water Solubility
- insoluble
- JECFA Number
- 1120 · 1120
- BRN
- 1741705 · 1741705
- Henry's Law Constant
- 1.2 · 1.2×10-1 mol/(m3Pa) at 25℃, Wu et al. (2022)
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3
- InChIKey
- UHEPJGULSIKKTP-UHFFFAOYSA-N
- SMILES
- C\C(C)=C\CCC(C)=O
- LogP
- 2.07 at · 2.07 at 25℃
- CAS DataBase Reference
- 110 · 110-93-0(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 6 · 6-METHYL-5-HEPTEN-2-ONE
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 448353 S93V · 448353S93V
- NIST Chemistry Reference
- 5 · 5-Hepten-2-one, 6-methyl-(110-93-0)
- EPA Substance Registry System
- 6 · 6-Methyl-5-hepten-2-one (110-93-0)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Warning
- Hazard statements
- 226 · H226
- Precautionary statements
- 210 · P210-P233-P240-P241-P242-P243
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- Risk Statements
- 10 · 10-36/37/38
- Safety Statements
- 16 · 16-24/25
- RIDADR
- 1224 · UN 1224 3/PG 3
- WGK Germany
- 1 · 1
- RTECS
- 9700000 · MJ9700000
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29141990 · 29141990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 · Flam. Liq. 3
- Toxicity
- 50 in · The acute oral LD50 in rats was reported as 3.5 g/kg (Br & Griepentrog, 1967) and as 4T g/kg (3.33-5.04 g/kg) (Keating, 1972). The acute dermal LD50 exceeded 5 g/kg (Keating, 1972).
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Warning
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P264+P265, P280, P303+P361+P353, P305+P351+P338, P337+P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1822 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1601) of reports.
Warning
Hazard information
Regulatory Information
Chemical: 5-Hepten-2-one, 6-methyl-
Chemical: Heptenone, methyl-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 27-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/12205
5-Hepten-2-one, 6-methyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
No sensitization when patch testing 3% in petrolatum on 25 volunteers; [HSDB]
No skin sensitization observed in study of 25 volunteers; [IUCLID] Mild skin irritation observed in rabbits (nearly reversed in 48 hours); Causes mild corneal opacity and mild conjunctival redness in rabbits 24 hours following application (completely reversed within 8 days); Not a skin sensitizer in guinea pigs; Significant effects to sperm, significantly increased absolute and relative liver and kidney weights, decreased size of the testes and epididymis, and histopathological changes of the liver, kidney, and testes observed in 90-day oral study of rats at the highest tested dose (1,000 mg/kg/day, with a LOAEL of 50 mg/kg/day); [OECD SIDS] Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Sigma-Aldrich MSDS]
FDA Requirements
21 CFR 172.515; SYNTHETIC FLAVOR & ADJUVANTS USEFUL IN CITRUS, BANANA, PEAR, BERRY
21 CFR 121.1164
NFPA Hazard Classification
1 - Materials that, under emergency conditions, can cause significant irritation.
2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.
0 - Materials that in themselves are normally stable, even under fire conditions.
Hazard Classes and Categories
Flam. Liq. 3 (100%)
Flam. Liq. 3 (98.2%)
Flammable liquids - Category 3
Safety & protection
Fire Fighting Procedures"ALCOHOL" FOAM.
Toxicology
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Natural Pollution SourcesORIGINALLY REPORTED IN LEMONGRASS. IT HAS BEEN FOUND IN THE ESSENTIAL OILS OF PALMAROSA, LEMON, CITRONELLA, VERVAIN, GERANIUM, OCIMUM CANUM, ARTEMISIA SCOPARIA, URTRIA DIOICA & OTHERS.
Human Toxicity Excerpts
TESTED AT 3% IN PETROLATUM, IT PRODUCED NO IRRITATION AFTER A 48-HR CLOSED-PATCH TEST ON HUMAN SUBJECTS. A MAXIMIZATION TEST WAS CARRIED OUT ON 25 VOLUNTEERS. THE MATERIAL WAS TESTED AT A CONCN OF 3% IN PETROLATUM & PRODUCED NO SENSITIZATION REACTIONS.
Non-Human Toxicity ExcerptsMETHYL HEPTENONE APPLIED FULL STRENGTH TO INTACT OR ABRADED RABBIT SKIN FOR 24 HR UNDER OCCLUSION WAS IRRITATING.
Toxicity DataLC50 (rat) > 13,960 mg/m3/4hr
Regulatory information
FDA Requirements
21 CFR 172.515; SYNTHETIC FLAVOR & ADJUVANTS USEFUL IN CITRUS, BANANA, PEAR, BERRY
21 CFR 121.1164
Safety data
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- MJ9700000
- ridadr
- UN 1224 3/PG 3
- hs_code
- 29141990
- Toxicity
- The acute oral LD50 in rats was reported as 3.5 g/kg (Br & Griepentrog, 1967) and as 4T g/kg (3.33-5.04 g/kg) (Keating, 1972). The acute dermal LD50 exceeded 5 g/kg (Keating, 1972).
- risk_code
- 10-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS02
- safety_code
- 16-24/25
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H226
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Flam. Liq. 3
- Precautionary statements
- P210-P233-P240-P241-P242-P243
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
Found in oil of lemon grass; Used in organic synthesis and in perfumes and flavoring; [Hawley]
Used as flavor enhancer; [FDA] Used mainly for chemical synthesis (closed systems); Also used in cleaning agents and as a flavor or aroma additive in cosmetics and food; [OECD SIDS]
ORGANIC SYNTHESIS; INEXPENSIVE PERFUMES; SYNTHETIC FLAVORING AGENT
FLAVORING AGENT IN NON-ALCOHOLIC BEVERAGES, IN ICE CREAM, ICES & CANDY, IN BAKED GOODS, IN GELATINS & PUDDINGS (ISOMERIC MIXT); CHEM INT FOR ISOMETHEPTENE (6-METHYL-5-HEPTEN-2-ONE) & VITAMIN A (6-METHYL-5-HEPTEN-2-ONE); FRAGRANCE (METHYLHEPTENONE & DERIVATIVES)
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1980) 9.98X10+6 G-PRINCPL CUSTMS DISTS (MIXT)
(1981) 9.11X10+6 G-PRINCPL CUSTMS DISTS (MIXT)
U.S. Production
(1978) MORE THAN 9.1X10+5 G (ISOMERIC MIXT)
(1979) MORE THAN 9.1X10+5 G (ISOMERIC MIXT)
Methods of Manufacturing
FROM OIL OF LEMON GRASS OR BY CONTROLLED OXIDATION OF CORRESPONDING SECONDARY ALCOHOL.
REFLUX OF LEMONGRASS OIL OR CITRAL IN AQUEOUS POTASSIUM CARBONATE FOLLOWED BY FRACTIONATION; REACTION OF ACETOACETIC ESTER & METHYLBUTEN-3-OL-2 WITH ALUMINUM ALCOHOLATE FOLLOWED BY PYROLYSIS OF THE ESTER
Household Products
Information on 6 consumer products that contain 6-Methyl-5-Hepten-2-One in the following categories is provided:
Information on 1 consumer products that contain Methylheptenone Isomers in the following categories is provided:
Use Classification
Fragrance Ingredients
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
5-Hepten-2-one, 6-methyl-: ACTIVE
Heptenone, methyl-: ACTIVE
METHYL HEPTENONE WAS GIVEN GRAS STATUS BY FEMA (1965) & IS APPROVED BY THE FDA FOR FOOD USE (21 CFR 121.1164). THE COUNCIL OF EUROPE (1974) INCL METHYL HEPTENONE AT A LEVEL OF 1 PPM IN THE LIST OF ARTIFICIAL FLAVORING SUBSTANCES THAT MAY BE ADDED TO FOODSTUFFS WITHOUT HAZARD TO PUBLIC HEALTH.
FEMA NUMBER: 2707 LIMITATIONS: SYNTHETIC FLAVOR.
USE IN FRAGRANCES IN THE USA AMOUNTS TO APPROX 2000 LB/YR. CONCN IN FINAL PRODUCT (%): SOAP: USUAL 0.01, MAX 0.05; DETERGENT: USUAL 0.001, MAX 0.005; CREAMS, LOTIONS: USUAL 0.005, MAX 0.03; PERFUME: USUAL 0.04, MAX 0.3.
WHEN TESTED AGAINST WIDE VARIETY OF BACTERIA & FUNGI, METHYL HEPTENONE DISPLAYED MARKED ANTIBACTERIAL ACTIVITY & ONLY VERY LIMITED ANTIFUNGAL ACTIVITY. IT WAS ACTIVE AGAINST ALL SPECIES EXCEPT BACILLUS SUBTILIS & BACILLUS ANTHRACIS.
Applications
Description6-Methyl-5-hepten-2-one has a strong, fatty, green, citrus-like odor, and a bittersweet taste reminiscent of pear. May be prepared from oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2C 03, and subsequent distillation and vacuum fractionation; from acetoacetic ester and methylbuten-3-ol-2 with aluminum alcoholate in Carroll’s reaction followed by pyrolysis of the ester.
OccurrenceOriginally identified in lemongrass; it has been reported found in the essential oils of palmarosa, lemon, citronella, vervain, geranium, Ocimum canum, Artemisia scoparia, Urtica dioica and others. Also reported found in apple, apricot, sweet and sour cherry, orange juice, citrus peel oils, bilberry, lingonberry, cranberry, guava, grapes, melon, peach, pear, raspberry, strawberry, blackberry, carrot, celery, tomato, potato, clove bud and leaf, ginger, peppermint oil, thymus, Gruyere cheese, butter, beef, hop oil, beer, cognac, cider, white wine, cocoa, tea, peanut oil, avocado, Arctic bramble, cloudberry, olive, passion fruit, plumcot, rose apple, marjoram, starfruit, mango, fig, rice, rice bran, quince, origanum, calamus, buckwheat, corn oil, wort, dried bonito, elderberry, cherimoya, kiwifruit, mountain papaya, endive, lemon balm, clary sage, nectarine, clam, Cape gooseberry, maté, German chamomile oil and mastic gum leaf oil, lime oil and apple brandy
Uses6-Methyl-hepten-2-one is used in the synthesis of thyrsiferyl 23-Acetate which acts as an anti-leukemic inducer of apoptosis.
UsesOrganic synthesis, inexpensive perfumes, fla-voring.
General Description6-Methyl-5-hepten-2-one is one of the main flavor volatile of tomatoes.
Preparation methods
PreparationFrom oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2CO3, and subsequent distillation and vacuum fractionation; from acetoacetic ester and methyl-buten-3-ol-2 with aluminum alcoholate in Carroll’s reaction followed by pyrolysis of the ester
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers15 total
Hebei baicao biology science and technology co., ltd+86-19131911055 17824879454 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
河北缤享新材料科技有限公司+8618633865755 · [email protected]
Hebei shenghao import and export trade co. LTD+8618431136903
普善实业（陕西）有限公司029-81310890 18165209495 · [email protected]
sgtlifesciences pvt ltd+91-8790379245 · [email protected]
深圳利斯康医药科技有限公司+86-755-89396905 +86-15013857715 · [email protected]
陕西缔都医药化工有限公司029-029-029-81148696 18161915376 · [email protected]
湖北美索伦科技有限公司13419562052 13419562052 · [email protected]
武汉卡米克科技有限公司18162538168 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
陕西缔都医药化工有限公司+86-29-87569266 +86-17392581500 · [email protected]
CD Chemical Group Limited+86-13651442114 · [email protected]
Additional notes
DefinitionChEBI: A heptenone that is hept-5-en-2-one substituted by a methyl group at position 6. It is a volatile oil component of citronella oil, lemon-grass oil and palmarosa oil.
Related reactions
25 records
Linked notes
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