γバレロラクトン

Gamma-Valerolactone

HCID 7921CAS 108-29-2
部分構造検索類似構造を探す

基本情報

標準SMILES
CC1CCC(=O)O1
InChIKey
GAEKPEKOJKCEMS-UHFFFAOYSA-N
分子式
C5H8O2
平均分子量
100.12 g/mol
単同位体質量
100.0524295

概要

Gamma-valerolactone is a clear, colorless, mobile liquid. pH (anhydrous): 7.0. pH (10% solution in distilled water): 4.2. (NTP, 1992)

名称と識別子

優先名称
Gamma-Valerolactone
IUPAC
5-methyloxolan-2-one
現地名
γバレロラクトン
英語名
γ-Valerolactone
分子式
C5H8O2
分子量
100.12

名称と別名

gamma-Valerolactone108-29-24-Pentanolide4-Valerolactonegamma-Pentalactone4-Hydroxypentanoic acid lactone4-Hydroxyvaleric acid lactone2(3H)-Furanone, dihydro-5-methyl-4-Methyl-gamma-butyrolactonegamma-Methyl-gamma-butyrolactone4-Methyl-4-hydroxybutanoic acid lactoneDIHYDRO-5-METHYL-2(3H)-FURANONE
名称をさらに表示
γバレロラクトン5-メチルジヒドロ-2(3H)-フラノン3,4-ジヒドロ-5-メチルフラン-2(5H)-オン5-メチル-4,5-ジヒドロフラン-2(3H)-オン5-メチルオキソラン-2-オン4-メチル-4-ヒドロキシ酪酸ラクトンγ-メチルブチロラクトンγ-メチル-γ-ブチロラクトン5-メチル-3,4-ジヒドロフラン-2(5H)-オン5-メチルジヒドロフラン-2(3H)-オンジヒドロ-5-メチルフラン-2(3H)-オン4,5-ジヒドロ-5-メチル-2(3H)-フラノンγ-バレロラクトン4,5-ジヒドロ-5-メチルフラン-2(3H)-オン4-ヒドロキシ吉草酸1,4-ラクトン5-メチルテトラヒドロフラン-2-オンγ-ペンタラクトン4-ペンタノリド4-ヒドロキシペンタン酸ラクトン5-メチル-4,5-ジヒドロ-2(3H)-フラノン5-Methyldihydrofuran-2(3H)-oneγ-PentalactoneFEMA 31035-methyl-dihydro-furan-2-oneγ-ValeroactoneG-VALEROLACTONE
5-Methyltetrahydro-2-furanoneFEMA No. 3103DTXSID00476185-Methyldihydro-2(3H)-furanoneValeric acid, 4-hydroxy-, gamma-lactonePentanoic acid, 4-hydroxy-, gamma-lactoneO7056XK37XDihydro-5-methylfuran-2(3H)-one

データベース識別子

CAS
108-29-2、57129-69-8
PubChem CID
7921
DTXSID
DTXSID0047618
ChEMBL
CHEMBL195593
ChEBI
CHEBI:48569
UNII
O7056XK37X
EC Number
203-569-5
Nikkaji
J5.072E

物性

構造計算による物性

XLogP
0.6
極性表面積
26.3 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
7

実験および物理化学的性質

Chemical ClassesOther Classes -> Lactones
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704]
FragrancesFragrance Ingredient (gamma-Valerolactone) -> IFRA transparency List
LogP-0.270
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 件

1.057 at 68 °F (NTP, 1992) - Denser than water; will sink

1.047-1.054

物理化学的性質

融点
31 °C · −31 °C(lit.)
沸点
207 · 207-208 °C(lit.)
比重(密度)
1.05 g/mL · 1.05 g/mL at 25 °C(lit.)
蒸気密度
3.45 · 3.45 (vs air)
蒸気圧
30 · 30-44Pa at 20-25℃
屈折率
20 · n20/D 1.432(lit.)

化学的性質

化学的特性γ-Valerolactone has a sweet, herbaceous odor.

安全と法規制

GHS分類

GHS Classification · 3 件

This chemical does not meet GHS hazard criteria for 96.7% (1420 of 1469) of all reports.

Not Classified

Aggregated GHS information provided per 1469 reports by companies from 9 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 4 件

Chemical: 2(3H)-Furanone, dihydro-5-methyl-

Regulation (EC) No 1831/2003 (amended)

Status: Active Update: 15-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/33023

2(3H)-Furanone, dihydro-5-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2(3H)-Furanone, dihydro-5-methyl-: Environment tier I assessment
DOT LabelFlammable Liquid
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract.
Hazards Summary · 1 件

A mild skin irritant; Causes general anesthesia in oral lethal-dose studies of rabbits and rats; [RTECS] A skin, eye, mucous membrane, and upper respiratory tract irritant; [NTP] Safe when used as a flavoring agent in food; [JECFA] An irritant; [Alfa Aesar MSDS] See Butyrolactones.

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Personal Protective Equipment (PPE) · 1 件

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

毒性情報

Adverse EffectsNeurotoxin - Acute solvent syndrome

安全データ

wgk
2
tsca
TSCA listed
rtecs
LU3580000
hs_code
29322980
risk_code
36-36/37/38
化審法
(9)-137

化学と産業

薬理情報

Cellular LocationsCytoplasm

用途と製造

Uses · 2 件

A metabolite of n-hexane; [ChemIDplus] Used as flavoring agent or adjuvant; [FDA] A constituent of crude polyligneous acid; Used in dye bathes (coupling agent), brake fluid, cutting oils, and as a solvent for adhesives, insecticides, and lacquers; [NTP]

Metal Machining [Category: Heat or Machine]

Household ProductsInformation on 2 consumer products that contain Gamma-Valerolactone in the following categories is provided:
Use Classification · 3 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information2(3H)-Furanone, dihydro-5-methyl-: ACTIVE
応用分野 · 6 件

解説4-あるいは5-ヒドロキシ吉草酸のOH基が，酸のCOOH基と分子内でエステル結合をつくって生じる環状エステル．五員環のγ-バレロラクトンおよび六員環のδ-バレロラクトンの2種がある．

説明γ-Valerolactone (Item No. 28240) is an analytical reference standard categorized as a prodrug form of γ-hydroxyvaleric acid (GHV; ). This product is intended for research and forensic applications.

天然物の起源Reported found in boiled beef, beef fat, beer, cacao, Swiss cheese, ground and roasted coffee, roasted filberts, milk fat, dried mushroom, peach, roasted peanuts, heated pork fat, black tea and yogurt. Also reported found in peach, strawberry jam, tomato, wheaten bread, Gruyere cheese, heated butter, cooked beef, white wine, red wine, coffee and Bourbon vanilla.

使用γ-Valerolactone is a naturally occurring chemical found in fruits and is frequently used as a food additive. It can be converted to liquid alkenes which can be used as transportation fuels. γ-Valerolactone is widely used in dye baths (coupling agent), brake fluids, cutting oils, and as solvent for adhesives, insecticides, and lacquers.

一般的な説明γ-Valerolactone has been identified as one of the volatile flavor constituents in mango and honey.

一般的な説明γ-Valerolactone(GVL) is a dipolar aprotic, bio-based, fully degradable, non-toxic green solvent and has been aligned with "Safer Solvent and Auxiliaries"," Use of Renewable Feedstocks and Design for Degradation".

調製方法 · 2 件

製造方法By reduction of levulinic acid followed by cyclization.

純化方法Purify the -lactone by repeated fractional distillation [Boorman & Linstead J Chem Soc 577, 580 1933]. IR: max 1790 (CS2), 1775 (CHCl3) cm-1 [Jones et al. Can J Chem 3 7 2007 1959]. The BF3-complex distils at 110-111o/20mm [Reppe et al. Justus Liebigs Ann Chem 596 179 1955]. It is characterized by conversion to -hydroxy-n-valeramide on treatment with NH3, m 51.5-52o (by slow evaporation of a CHCl3 solution). [Beilstein 17 H 235, 17 I 131, 17 II 288, 17 III/IV 4176, 17/9 V 24.]

上流・下流製品情報

サプライヤー1 社

HONEST JOY HOLDINGS LIMITED[email protected]

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