Grundinformationen
- Standard-SMILES
CC(=O)CCC=C(C)C- InChIKey
UHEPJGULSIKKTP-UHFFFAOYSA-N- Summenformel
- C8H14O
- Durchschnittliche Molmasse
- 126,2 g/mol
- Monoisotopische Masse
- 126,10446507
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- 6-Methyl-5-hepten-2-one
- IUPAC
- 6-methylhept-5-en-2-one
- Lokaler Name
- 6-Methylhept-5-en-2-on
- Englischer Name
- 6-Methyl-5-hepten-2-one
- Summenformel
- C8H14O
- Molmasse
- 126.2
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,9
- Polarare Oberfläche (TPSA)
- 17,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 119
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Other Classes -> Aliphatic Ketones, Other
Other Classes -> Aliphatic Ketones, Other
Fragrances
Fragrance Ingredient (6-Methyl-5-hepten-2-one) -> IFRA transparency List
Fragrance Ingredient (Methylheptenone (isomer unspecified)) -> IFRA transparency List
Density
0.8546 @ 16 °C/4 °C
0.846-0.854
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)
Physikochemische Eigenschaften
- Schmelzpunkt
- -67.1 °C · -67.1 °C
- Siedepunkt
- 73 °C18 · 73 °C18 mm Hg(lit.)
- Dichte
- 0.855 g/mL · 0.855 g/mL at 25 °C(lit.)
- Dampfdruck
- 1.121 hPa · 1.121hPa at 20℃
- FEMA
- 2707 · 2707 | 6-METHYL-5-HEPTEN-2-ONE
- Brechungsindex
- 20 · n20/D 1.439(lit.)
- Flammpunkt
- 123 °F · 123 °F
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- Soluble in methanol and chloroform.
- Aggregatzustand
- Liquid
- Farbe
- Colorless to Light yellow
- Wichte
- 0.855 · 0.855
- PH
- 6.6 · 6.6 (3g/l, H2O, 25℃)
- Geruch (Odor)
- 10 % · at 10.00 % in dipropylene glycol. citrus green musty lemongrass apple
- Geruchsart
- citrus
- Biologische Quelle
- synthetic
- Explosionsgrenze
- 1.1 · 1.1-7.3%(V)
- Wasserlöslichkeit
- 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
- Kosmetik-Inhaltsstoffe Funktionen
- 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 Datenbank
- 110 · 110-93-0(CAS DataBase Reference)
- NIST chemische Informationen
- 5 · 5-Hepten-2-one, 6-methyl-(110-93-0)
- EPA chemische Informationen
- 6 · 6-Methyl-5-hepten-2-one (110-93-0)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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
Gefahrenhinweise
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
Sicherheit und Schutzausrüstung
Toxikologische Informationen
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.
Regulatorische Informationen
FDA Requirements
21 CFR 172.515; SYNTHETIC FLAVOR & ADJUVANTS USEFUL IN CITRUS, BANANA, PEAR, BERRY
21 CFR 121.1164
Sicherheitsdaten
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 1224 3/PG 3
- hs_code
- 29141990
- RTECS-Nr.
- MJ9700000
- risk_code
- 10-36/37/38
- Toxizität
- 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).
- safety_code
- 16-24/25
- hazard_class
- 3
- packing_group
- III
- Speicherklasse
- 3 - Flammable liquids
- Hazard Classifications
- Flam. Liq. 3
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
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.
Anwendungen
Beschreibung6-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
VerwendenOrganic synthesis, inexpensive perfumes, fla-voring.
Darstellung
synthetischeFrom 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
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter15 Anbieter
Ergänzende Hinweise
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.
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