γバレロラクトン
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
識別子と物理属性
| CAS No. | 108-29-2 |
|---|---|
| 分子式 | C5H8O2 |
| 平均分子量 | 100.12 g/mol |
| 単同位体質量 | 100.0524295 g/mol |
| SMILES | CC1CCC(=O)O1 |
| InChIKey | GAEKPEKOJKCEMS-UHFFFAOYSA-N |
| PubChem CID | 7921 |
| ChEMBL | CHEMBL195593 |
| ChEBI | CHEBI:48569 |
| EC No. | 203-569-5 |
| DTXSID | DTXSID0047618 |
| 現地名 | γバレロラクトン |
化学・物理的性質
| XLogP | 0.6 |
|---|---|
| 極性表面積 | 26.3 |
| 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 |
| 形式電荷 | 0 |
| 複雑度 | 88.1 |
| 物質分類 | Other Classes -> Lactones |
| 脂質 | Fatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704] |
| 香料 | Fragrance Ingredient (gamma-Valerolactone) -> IFRA transparency List |
| LogP（分配係数） | -0.270 |
| 食品添加物 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 密度 | 1.057 at 68 °F (NTP, 1992) - Denser than waterwill sink1.047-1.0541.05 g/mL at 25 °C(lit.) |
| 香味料 | EU Flavoring substances |
| 溶解度 | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)miscible with alcohol, most fixed oils and water(in ethanol)クロロホルム、メタノール混和性 |
| 引火点 | 178 °F (NTP, 1992)204.8 °F |
| 沸点 | 405 to 406 °F at 760 mmHg (NTP, 1992)207.00 to 208.00 °C. @ 760.00 mm Hg207 °C207-208 °C(lit.) |
| 融点 | -24 °F (NTP, 1992)-31 °C−31 °C(lit.) |
| 蒸気密度 | 3.45 (NTP, 1992) - Heavier than airwill sink (Relative to Air)3.45 (vs air) |
| 蒸気圧 | 30-44Pa at 20-25℃ |
| 屈折率 | n20/D 1.432(lit.) |
| FEMA | 3103 | GAMMA-VALEROLACTONE |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | 液体 |
| 色 | 無色透明 |
| pH | 7 (H2O, 20℃) |
| 臭い | 100.00%で。ハーブの甘い温かいタバコココアウッディ |
| においのタイプ | ハーブ |
| 由来生物 | synthetic |
| JECFA Number | 220 |
| BRN | 80420 |
| 誘電率 | 36.140000000000001 |
| 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/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3 |
| InChIKey | GAEKPEKOJKCEMS-UHFFFAOYSA-N |
| SMILES | CC1CCC(=O)O1 |
| LogP（分配係数） | -0.27 |
| CAS データベース | 108-29-2(CAS DataBase Reference) |
| NISTの化学物質情報 | 2(3H)-Furanone, dihydro-5-methyl-(108-29-2) |
| EPAの化学物質情報 | 2(3H)-Furanone, dihydro-5-methyl- (108-29-2) |
化学的特性
γ-Valerolactone has a sweet, herbaceous odor.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 96.7% (1420 of 1469) of all reports.Not ClassifiedAggregated GHS information provided per 1469 reports by companies from 9 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | 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/330232(3H)-Furanone, dihydro-5-methyl-: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - 2(3H)-Furanone, dihydro-5-methyl-: Environment tier I assessment |
| 輸送ラベル（DOT） | Flammable Liquid |
| 火災危険 | This chemical is combustible. (NTP, 1992) |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. |
| 有害性の概要 | A mild skin irritantCauses 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. |
| 反応性グループ | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Reactivity Profile | GAMMA-VALEROLACTONE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. This chemical is incompatible with strong oxidizers. (NTP, 1992). This chemical is incompatible with strong oxidizing agents. It is also incompatible with strong acids, strong bases and strong reducing agents. (NTP, 1992). |
| Air and Water Reactions | Water soluble. |
| Hazard Classes and Categories | Not Classified |
| 消火 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| 応急処置 | 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. |
| 非火災時の漏出対応 | 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 Evacuation | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| Personal Protective Equipment (PPE) | 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) |
| 有害作用 | Neurotoxin - Acute solvent syndrome |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | LU3580000 |
| 税関コード | 29322980 |
| 危険文句（R） | 36-36/37/38 |
| 化審法 | (9)-137 |
| 消防法 | 危-4-3-III |
| 危険表示 | Xi |
| 安全措置（S） | 39-26-37/39 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2 |
| 貯蔵分類 | 10 - Combustible liquids |
用途
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".
製法・合成法
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.]