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2-メチル-2-ヘプテン-6-オン

6-Methyl-5-hepten-2-one

HCID 9862
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印刷プレビュー
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
110-93-0
標準SMILES
CC(=O)CCC=C(C)C
InChIKey
UHEPJGULSIKKTP-UHFFFAOYSA-N
分子式
C8H14O
平均分子量
126.2 g/mol
単同位体質量
126.10446507

概要

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.

名称と識別子

優先名称
6-Methyl-5-hepten-2-one
IUPAC
6-methylhept-5-en-2-one
現地名
2-メチル-2-ヘプテン-6-オン
英語名
6-Methyl-5-hepten-2-one
分子式
C8H14O
分子量
126.2

名称と別名

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
名称をさらに表示
2-メチル-2-ヘプテン-6-オンスルカトンプレニルアセトンメチルヘプテノン6-メチル-5-ヘプテン-2-オン６メチル５ヘプテン２オン6‐メチル‐5‐ヘプテン‐2‐オン6-メチルヘプト-5-エン-2-オン6-メチル-5-ヘプテン-2-オン, 98%6-メチルヘプタ-5-エン-2-オン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

データベース識別子

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

物性

構造計算による物性

XLogP
1.9
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
3
重原子数
9
形式電荷
0
複雑度
119

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Aliphatic Ketones, Other

Other Classes -> Aliphatic Ketones, Other

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

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 件

0.8546 @ 16 °C/4 °C

0.846-0.854

Flavoring AgentsEU Flavoring substances
Color/FormCOLORLESS LIQUID
Solubility · 4 件

INSOL IN WATER; SOL IN ALL PROP WITH ALCOHOL, ETHER

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

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

危険有害性情報

Regulatory Information · 5 件

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 件

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 · 2 件

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

化学と産業

薬理情報

Cellular LocationsCytoplasm

用途と製造

Uses · 4 件

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 件

(1979) No Data

(1981) No Data

U.S. Imports · 2 件

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

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

U.S. Production · 2 件

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

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

Methods of Manufacturing · 2 件

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 件

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

関連反応

25 件
反応記録を作成
HRID 46463 の反応式
HRID 46463生成物としてuspto-grants-1979_11
HRID 46464 の反応式
HRID 46464生成物として反応物としてuspto-grants-1979_11
HRID 299506 の反応式
HRID 299506生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 513976 の反応式
HRID 513976反応物としてuspto-grants-2015_08
HRID 618862 の反応式
HRID 618862生成物としてuspto-grants-1999_09
HRID 686345 の反応式
HRID 686345反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 718515 の反応式
HRID 718515反応物としてuspto-grants-2015_11
HRID 926409 の反応式
HRID 926409反応物としてuspto-grants-2016_03
1 / 4 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す

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)

物理化学的性質

融点
-67.1 °C · -67.1 °C
沸点
73 °C18 · 73 °C18 mm Hg(lit.)
比重(密度)
0.855 g/mL · 0.855 g/mL at 25 °C(lit.)
蒸気圧
1.121 hPa · 1.121hPa at 20℃
FEMA
2707 · 2707 | 6-METHYL-5-HEPTEN-2-ONE
屈折率
20 · n20/D 1.439(lit.)
闪点
123 °F · 123 °F
貯蔵温度
2 · Sealed in dry,2-8°C
溶解性
メタノール、クロロホルムに可溶。
外見
Liquid
色
Colorless to Light yellow
比重
0.855 · 0.855
PH
6.6 · 6.6 (3g/l, H2O, 25℃)
臭い (Odor)
10 %。シトラスグリーンかび臭いレモングラスアップル · ジプロピレングリコール中10.00%。シトラスグリーンかび臭いレモングラスアップル
においのタイプ
柑橘類
由来生物
synthetic
爆発限界(explosive limit)
1.1 · 1.1-7.3%(V)
水溶解度
不溶性
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)
主な用途
フレーバーそして香料
化粧品成分の機能
香料
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 データベース
110 · 110-93-0(CAS DataBase Reference)
NISTの化学物質情報
5 · 5-Hepten-2-one, 6-methyl-(110-93-0)
EPAの化学物質情報
6 · 6-Methyl-5-hepten-2-one (110-93-0)
化学的性質 · 1 件

化学的特性6-Methyl-5-hepten-2-one is an important intermediate in the synthesis of terpenoids. Its odor properties are not impressive. It occurs in nature as a degradation product of terpenes. (Z)- and (E)-Tagetone, [3588-18-9], [6752-80-3], are major components of tagetes oil. Solanone [1937-54-8] and pseudoionone [141-10-6] are acyclicC13 ketoneswith a terpenoid skeleton. Solanone is one of the flavor-determining constituents of tobacco, and pseudoionone is an intermediate in the synthesis of ionones.

21 CFR 121.1164

NFPA Hazard Classification · 3 件

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 件

Flam. Liq. 3 (100%)

Flam. Liq. 3 (98.2%)

Flammable liquids - Category 3

安全と保護具

Fire Fighting Procedures"ALCOHOL" FOAM.

毒性情報

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 件

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

法規制情報

FDA Requirements · 2 件

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

21 CFR 121.1164

安全データ

wgk
1
tsca
TSCA listed
rtecs
MJ9700000
ridadr
UN 1224 3/PG 3
毒性
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).
hs_code
29141990
risk_code
10-36/37/38
化審法
(2)-2480
消防法
危-4-2-III
safety_code
16-24/25
hazard_class
3
packing_group
III
Hazard Classifications
Flam. Liq. 3
ストレージクラス
3 - Flammable liquids
· 5 件

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 件

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.

応用分野 · 6 件

用途医薬品の合成中間体。

用途ビタミン、香料、医薬品等ファインケミカルの中間原料。食品、化粧品等の芳香剤添加成分

説明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.

天然物の起源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

使用Organic synthesis, inexpensive perfumes, fla-voring.

一般的な説明6-Methyl-5-hepten-2-one is one of the main flavor volatile of tomatoes.

調製方法 · 1 件

製造方法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

上流・下流製品情報

上流原料

イソプレン6-メチル-6-ヘプテン-2-オン6-メチル-2-ヘプタノン

下流製品

ヘプタミノールリナロールシトラール (cis-, trans-混合物)3,7-ジメチル-2,6-オクタジエン酸3,7-ジメチル-1-オクテン-3-オール6-メチル-2-ヘプタノール3,7-ジメチル-2,6-オクタジエン酸エチル

補足説明

定義ChEBI: 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.