6-Methylhept-5-en-2-on
METHYL HEPTENONE · sulcatone · 6-METHYL-5-HEPTENE-2-ONE · 2-METHYL-2-HEPTEN-6-ONE · FEMA 2707 · methyl-5-hepten-2-one · 5-Hepten-2-one,6-methyl- · Methyl hepten
Identifikatoren & physikalische Daten
| CAS No. | 110-93-0 |
|---|---|
| Summenformel | C8H14O |
| Durchschnittliche Molmasse | 126,2 g/mol |
| Monoisotopische Masse | 126,10446507 g/mol |
| SMILES | CC(=O)CCC=C(C)C |
| InChIKey | UHEPJGULSIKKTP-UHFFFAOYSA-N |
| PubChem CID | 9862 |
| ChEMBL | CHEMBL46340 |
| ChEBI | CHEBI:16310 |
| EC No. | 203-816-7 |
| DTXSID | DTXSID5021629 |
| Lokaler Name | 6-Methylhept-5-en-2-on |
Chemische & physikalische Eigenschaften
| XLogP | 1,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 119 |
| Stoffklassen | Other Classes -> Aliphatic Ketones, Other |
| Lipide | Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12] |
| SpringerMaterials Properties | Boiling point |
| Duftstoffe | Fragrance Ingredient (6-Methyl-5-hepten-2-one) -> IFRA transparency ListFragrance Ingredient (Methylheptenone (isomer unspecified)) -> IFRA transparency List |
| Geruch | POWERFUL, FATTY, GREEN, CITRUS ODOR |
| Geschmack | FRUITY TASTE |
| Lebensmittelzusatzstoffe | FLAVOR ENHANCER -> FDA Substance added to food |
| Dichte | 0.8546 @ 16 °C/4 °C0.846-0.8540.855 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | COLORLESS LIQUID |
| Löslichkeit | INSOL IN WATERSOL IN ALL PROP WITH ALCOHOL, ETHER3351 /mg/L @ 20 °C (exp)Insoluble in watersoluble in oils and organic solventsMiscible at room temperature (in ethanol)Soluble in methanol and chloroform. |
| Flammpunkt | 135 °F (57 °C)123 °F |
| Schmelzpunkt | -67.1 °C |
| Siedepunkt | 73 °C18 mm Hg(lit.) |
| Dampfdruck | 1.121hPa at 20℃ |
| FEMA | 2707 | 6-METHYL-5-HEPTEN-2-ONE |
| Brechungsindex | n20/D 1.439(lit.) |
| Lagerbedingungen | Sealed in dry,2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Colorless to Light yellow |
| Wichte | 0.855 |
| pH | 6.6 (3g/l, H2O, 25℃) |
| Geruch | at 10.00 % in dipropylene glycol. citrus green musty lemongrass apple |
| Geruchsart | citrus |
| Biologische Quelle | synthetic |
| Explosionsgrenze | 1.1-7.3%(V) |
| JECFA Number | 1120 |
| BRN | 1741705 |
| Henry-Konstante | 1.2×10-1 mol/(m3Pa) at 25℃, Wu et al. (2022) |
| Hauptanwendungen | 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 (Verteilungskoeffizient) | 2.07 at 25℃ |
| CAS Datenbank | 110-93-0(CAS DataBase Reference) |
| NIST chemische Informationen | 5-Hepten-2-one, 6-methyl-(110-93-0) |
| EPA chemische Informationen | 6-Methyl-5-hepten-2-one (110-93-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH226 (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. |
|---|---|
| Regulatorische Informationen | 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/122055-Hepten-2-one, 6-methyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | 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 pigsSignificant 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-Anforderungen | 21 CFR 172.515SYNTHETIC FLAVOR & ADJUVANTS USEFUL IN CITRUS, BANANA, PEAR, BERRY21 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 |
| Brandbekämpfungsverfahren | "ALCOHOL" FOAM. |
| Unerwünschte Wirkungen | Occupational 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 Sources | ORIGINALLY 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 Excerpts | METHYL HEPTENONE APPLIED FULL STRENGTH TO INTACT OR ABRADED RABBIT SKIN FOR 24 HR UNDER OCCLUSION WAS IRRITATING. |
| Toxicity Data | LC50 (rat) > 13,960 mg/m3/4hr |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1224 3/PG 3 |
| Zollcode | 29141990 |
| RTECS-Nr. | MJ9700000 |
| R-Sätze (R) | 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). |
| Sicherheitshinweise (S) | 16-24/25 |
| Gefahrenklasse | 3Flam. Liq. 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Beschreibung
6-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.
Occurrence
Originally 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
Verwenden
Organic synthesis, inexpensive perfumes, fla-voring.
Herstellung & Synthese
synthetische
From 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