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6-Methylhept-5-en-2-on

6-Methyl-5-hepten-2-one

HCID 9862
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Grundinformationen

CAS
110-93-0
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

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

CAS
110-93-0、409-02-9
PubChem CID
9862
DTXSID
DTXSID5021629
ChEMBL
CHEMBL46340
ChEBI
CHEBI:16310
UNII
448353S93V

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 · 2 Einträge

Other Classes -> Aliphatic Ketones, Other

Other Classes -> Aliphatic Ketones, Other

LipidsFatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SpringerMaterials PropertiesBoiling point
Fragrances · 2 Einträge

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 · 2 Einträge

0.8546 @ 16 °C/4 °C

0.846-0.854

Flavoring AgentsEU Flavoring substances

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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 · 5 Einträge

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 · 2 Einträge

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]

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 4 Einträge

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 · 2 Einträge

(1979) No Data

(1981) No Data

U.S. Imports · 2 Einträge

(1980) 9.98X10+6 G-PRINCPL CUSTMS DISTS (MIXT)

(1981) 9.11X10+6 G-PRINCPL CUSTMS DISTS (MIXT)

U.S. Production · 2 Einträge

(1978) MORE THAN 9.1X10+5 G (ISOMERIC MIXT)

(1979) MORE THAN 9.1X10+5 G (ISOMERIC MIXT)

Methods of Manufacturing · 2 Einträge

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 · 2 Einträge

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:

Zugehörige Reaktionen

25
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 46463
HRID 46463als Produktuspto-grants-1979_11
Reaktionsgleichung von HRID 46464
HRID 46464als Produktals Eduktuspto-grants-1979_11
Reaktionsgleichung von HRID 299506
HRID 299506als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 513976
HRID 513976als Eduktuspto-grants-2015_08
Reaktionsgleichung von HRID 618862
HRID 618862als Produktuspto-grants-1999_09
Reaktionsgleichung von HRID 686345
HRID 686345als EduktTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
Reaktionsgleichung von HRID 718515
HRID 718515als Eduktuspto-grants-2015_11
Reaktionsgleichung von HRID 926409
HRID 926409als Eduktuspto-grants-2016_03
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EC Number
203-816-7、206-990-2
Nikkaji
J58.156I
Color/Form
COLORLESS LIQUID
Solubility · 4 Einträge

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)

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)
FDA Requirements · 2 Einträge

21 CFR 172.515; SYNTHETIC FLAVOR & ADJUVANTS USEFUL IN CITRUS, BANANA, PEAR, BERRY

21 CFR 121.1164

NFPA Hazard Classification · 3 Einträge

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 · 3 Einträge

Flam. Liq. 3 (100%)

Flam. Liq. 3 (98.2%)

Flammable liquids - Category 3

Sicherheit und Schutzausrüstung

Fire Fighting Procedures"ALCOHOL" FOAM.

Toxikologische Informationen

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 · 1 Eintrag

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

Regulatorische Informationen

FDA Requirements · 2 Einträge

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
Use Classification · 5 Einträge

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 · 6 Einträge

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 · 3 Einträge

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 · 1 Eintrag

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

Isopren6-methyl-6-hepten-2-one6-Methylheptan-2-on

Nachgelagerte Produkte

HeptaminolLinaloolCitral3,7-Dimethylocta-2,6-diensure3,7-Dimethyloct-1-en-3-ol6-Methylheptan-2-olEthyl-3,7-dimethylocta-2,6-dienoat

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.