2-ヒドロキシ-3-メチル-2-シクロペンテノン

2-Hydroxy-3-methyl-2-cyclopenten-1-one

HCID 6660CAS 80-71-7

基本情報

標準SMILES
CC1=C(O)C(=O)CC1
InChIKey
CFAKWWQIUFSQFU-UHFFFAOYSA-N
分子式
C6H8O2
平均分子量
112.13 g/mol
単同位体質量
112.0524295

概要

Cyclotene is a metabolite found in or produced by Saccharomyces cerevisiae.

名称と識別子

優先名称
2-Hydroxy-3-methyl-2-cyclopenten-1-one
IUPAC
2-hydroxy-3-methylcyclopent-2-en-1-one
現地名
2-ヒドロキシ-3-メチル-2-シクロペンテノン
英語名
Methyl cyclopentenolone
分子式
C6H8O2
分子量
112.13

名称と別名

80-71-7CycloteneCorylone2-HYDROXY-3-METHYL-2-CYCLOPENTEN-1-ONE2-hydroxy-3-methylcyclopent-2-en-1-oneCycloten2-Cyclopenten-1-one, 2-hydroxy-3-methyl-2-Hydroxy-1-methylcyclopenten-3-oneCyclotene (ordorant)NSC-133445627E92X64BFEMA No. 2700
名称をさらに表示
2-ヒドロキシ-3-メチル-2-シクロペンテノンコリロンマプルラクトン3-メチル-2-ヒドロキシ-2-シクロペンテン-1-オンメチルシクロペンテノロンシクロテン2-ヒドロキシ-3-メチル-2-シクロペンテン-1-オン1-メチル-2-ヒドロキシシクロペンテン-3-オン2-ヒドロキシ-3-メチルシクロペンタ-2-エノン3-メチル-2-シクロペンテノン-2-オール1-メチル-2-ヒドロキシ-3-オキソ-シクロペンテン2‐ヒドロキシ‐3‐メチル‐2‐シクロペンテノンFEMA 27002-HYDROXY-3-METHYL-2-CYCLOPENTENONE
DTXSID4035128RefChem:581283DTXCID2015128201-303-2Methylcyclopentenolone2-Hydroxy-3-methylcyclopent-2-enoneCorylonMaple lactone

データベース識別子

CAS
80-71-7
PubChem CID
6660
DTXSID
DTXSID4035128
UNII
627E92X64B
EC Number
201-303-2
Nikkaji
J10.510D

物性

構造計算による物性

XLogP
0.3
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
0
重原子数
8

実験および物理化学的性質

Chemical ClassesOther Classes -> Other Organic Compounds
FragrancesFragrance Ingredient (Methylcyclopentenolone) -> IFRA transparency List
Flavoring AgentsEU Flavoring substances
Physical DescriptionCBI; Large Crystals

物理化学的性質

融点
104 · 104-108°C
沸点
170.05 °C · 170.05°C (rough estimate)
比重(密度)
1.0795 · 1.0795 (rough estimate)
蒸気圧
2.1 hPa · 2.1hPa at 20℃
FEMA
2700 · 2700 | METHYLCYCLOPENTENOLONE
屈折率
1.4532 · 1.4532 (estimate)
化学的性質 · 1 件

化学的特性Methyl cyclopentenolone occurs in beechwood tar and has a caramel-like (burnt sugar) odor. It has been identified as a flavor component in food. Crystals of the compound usually contain 1 mol of water. Synthetic routes of production are of limited importance in comparison with isolation from beechwood tar. Homologs of cyclotene such as 3-ethyl-2-hydroxy-2-cyclopenten-1-one, C7H10O2, Mr 126.16, 2-hydroxy-3,4-dimethyl-2-cyclopenten-1-one, C7H10O2, Mr 126.16, and 2-hydroxy-3,5-dimethyl-2-cyclopenten-1-one, C7H10O2, Mr 126.16, are also used as flavor ingredients and have similar caramel-like properties. Cyclotene and its homologs are frequently used in flavor compositions for its caramel note, for example, in beverages and in confectionery.

安全と法規制

GHS分類

GHS Classification · 2 件

Not Classified

Aggregated GHS information provided per 1763 reports by companies from 8 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 5 件

Chemical: 2-Cyclopenten-1-one, 2-hydroxy-3-methyl-

Regulation (EC) No 1831/2003 (amended)

2-Cyclopenten-1-one, 2-hydroxy-3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Cyclopenten-1-one, 2-hydroxy-3-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: 2-hydroxy-3-methylcyclopent-2-enone (EC: 201-303-2)

Cylcotene: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySee 2-Pentyl-2-cyclopenten-1-one.
Hazard Classes and CategoriesNot Classified

安全データ

wgk
3
tsca
TSCA listed
rtecs
GY7298000
hs_code
29144090
risk_code
36/37/38-43
化審法
(3)-2406

化学と産業

用途と製造

UsesActive product registrations in the US for use in insect traps; [NPIRS] Product of sugar degradation. [ChemIDplus] Product category is Analytical/Chromatography and Flavors and Fragrances. [Sigma-Aldrich]
U.S. Production2023: <75,000 lb
Consumer UsesFragrance
Industry UsesFragrance
Household ProductsInformation on 5 consumer products that contain 2-Hydroxy-3-methylcyclopent-2-enone in the following categories is provided:
Use Classification · 5 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

応用分野 · 4 件

用途カスタードプリンのカラメルソース部分に似た、甘く焦げたにおいがあることから、食品や飼料添加物、衣料用洗剤、 電子たばこの香料として幅広く使用されている。また、日本の環境省告示の「臭気指数及び臭気排出強度の算定の方法」における基準臭液に採用されている。木材の薫煙処理により生じ、殺菌?防腐効果をもたらすとの説もある。

天然物の起源Reported to be found during the dry distillation of wood and in the corresponding tar oil. It has also been identified in fenugreek (FenaroWs Handbook of Flavor Ingredients, 1975).

使用Methyl Cyclopentenolone is a flavoring agent that is a white crys- talline powder. it has a nutty odor suggesting a maple-licorice aroma when diluted. it is soluble in alcohol and propylene glycol, slightly soluble in most fixed oils, and sparingly soluble in water. it is obtained by synthesis. it is also termed 3-methyl-cyclopentane-1,2-dione.

一般的な説明Methyl cyclopentenolone is one of the flavor compounds of maple syrup, coffee oil and wood smoke. It is reported to be one the key aroma compounds in Wasanbon sugar, contributing to the maple-like flavor. Methyl cyclopentenolone is also one of the major volatile compound formed during the thermal degradation of glucose.

調製方法

製造方法By ketonic hydrolysis of the corresponding dicarboxylic ester (Arctander, 1969)

サプライヤー50 社

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