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6-Methyl-5-hepten-2-one

HCID 9862
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Basic information

CAS
110-93-0
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 · 2 items

Other Classes -> Aliphatic Ketones, Other

Other Classes -> Aliphatic Ketones, Other

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

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 items

0.8546 @ 16 °C/4 °C

0.846-0.854

Flavoring AgentsEU Flavoring substances

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 · 6 items

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 · 5 items

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 items

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

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 4 items

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 items

(1979) No Data

(1981) No Data

U.S. Imports · 2 items

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

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

U.S. Production · 2 items

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

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

Methods of Manufacturing · 2 items

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 items

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:

Related reactions

25 records
New reaction record
HRID 46463 reaction equation
HRID 46463As productuspto-grants-1979_11
HRID 46464 reaction equation
HRID 46464As productAs reactantuspto-grants-1979_11
HRID 299506 reaction equation
HRID 299506As productTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 513976 reaction equation
HRID 513976As reactantuspto-grants-2015_08
HRID 618862 reaction equation
HRID 618862As productuspto-grants-1999_09
HRID 686345 reaction equation
HRID 686345As reactantTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 718515 reaction equation
HRID 718515As reactantuspto-grants-2015_11
HRID 926409 reaction equation
HRID 926409As reactantuspto-grants-2016_03
Page 1 of 4

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Color/Form
COLORLESS LIQUID
Solubility · 4 items

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)
· 2 items

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

21 CFR 121.1164

NFPA Hazard Classification · 3 items

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 items

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 · 1 item

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 · 2 items

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
Use Classification · 5 items

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 items

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 · 5 items

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 · 1 item

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

Isoprene6-methyl-6-hepten-2-one6-Methyl-2-heptanone

Downstream products

6-Amino-2-methyl-2-heptanolLinaloolCitralGeranic acid3,7-Dimethyl-1-octen-3-ol6-Methyl-2-heptanolEthyl geranate

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.