乙酰丙酸

Levulinic Acid

HCID 11579CAS 123-76-2
子结构检索查找相似结构

基本信息

标准SMILES
CC(=O)CCC(=O)O
InChIKey
JOOXCMJARBKPKM-UHFFFAOYSA-N
分子式
C5H8O3
平均分子量
116.11 g/mol
单同位素质量
116.04734412

概述

4-oxopentanoic acid is an oxopentanoic acid with the oxo group in the 4-position. It has a role as a plant metabolite. It is an oxopentanoic acid and a straight-chain saturated fatty acid. It is a conjugate acid of a 4-oxopentanoate.

名称与标识

首选名称
Levulinic Acid
IUPAC
4-oxopentanoic acid
中文名
乙酰丙酸
英文名
Levulinic acid
分子式
C5H8O3
分子量
116.12

名称与别名

LEVULINIC ACID4-Oxopentanoic acid123-76-2Laevulinic acidPentanoic acid, 4-oxo-4-Oxovaleric acidLevulic acid4-Ketovaleric acidgamma-Ketovaleric acidLEVAAcetopropionic acidLevulinsaeure
展开更多名称
果糖酸左旋酸左乙酸乙醯丙酸果糖衍酸左旋糖酸乙酰丙酸Y-戊酮酸二十四烷醇Γ-酮戊酸LAlevulinicAcetylpropionic acidFEMA 26272-KETOVALERIC ACID
Laevulic acidbeta-Acetylpropionic acidAcidum laevulinicumFEMA No. 2627DTXSID8021648RYX5QG61EINSC-3716DTXCID701648

数据库标识

CAS
123-76-2
PubChem CID
11579
DTXSID
DTXSID8021648
ChEMBL
CHEMBL1235931
ChEBI
CHEBI:45630
UNII
RYX5QG61EI
EC Number
204-649-2
Nikkaji
J10.067F

性质

结构计算性质

XLogP
-0.5
极性表面积
54.4 Ų
氢键供体
1
氢键受体
3
可旋转键
3
重原子
8

实验与物化性质

Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Oxo fatty acids [FA0106]
Cosmetics · 2 条

Cosmetic ingredients (Levulinic Acid) -> CIR (Cosmetic Ingredient Review)

Skin conditioning

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Levulinic acid) -> IFRA transparency List

物理化学性质

熔点
30 · 30-33 °C (lit.)
沸点
245 · 245-246 °C (lit.)
密度
1.134 g/mL · 1.134 g/mL at 25 °C (lit.)
蒸气压
1 mm · 1 mm Hg ( 102 °C)
折射率
20 · n20/D 1.439(lit.)
FEMA
2627 · 2627 | LEVULINIC ACID

化学性质

白色片状结晶，有吸湿性。 易溶于水和醇、醚类有机溶剂。

安全与法规

GHS分类

GHS Classification · 4 条

Danger

H302 (99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P305+P354+P338, P317, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1892 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危害信息

Regulatory Information · 5 条

Chemical: Pentanoic acid, 4-oxo-

Regulation (EC) No 1831/2003 (amended)

Pentanoic acid, 4-oxo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pentanoic acid, 4-oxo- 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)

Status: Active Update: 06-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17335

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

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryA moderate skin irritant; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; Harmful by ingestion; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (99.9%)

毒理信息

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

安全数据

wgk
3
tsca
TSCA listed
毒性
LD50 orally in Rabbit: 1850 mg/kg LD50 dermal Rabbit > 5000 mg/kg
RTECS号
OI1575000
包装类别
III
危险等级
8

毒性防护

毒性GRAS(FEMA)。

化学与工业

药理信息

MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Tissue LocationsNeuron
Cellular LocationsCytoplasm

用途与制造

Uses · 3 条

CIR ingredient: Levulinic Acid

Used to make nylon, synthetic rubber, plastic, and medicinals; [Merck Index] Used as a flavoring agent; [FDA] Used to flavor animal feeds; [ExPub: EFSA - FEEDAP]

Farming (Feed Additives) [Category: Industry]

U.S. Production2023: 50,000 - <250,000 lb
Consumer UsesIntermediate
Industry UsesLaboratory chemicals
Household ProductsInformation on 1 consumer products that contain Levulinic Acid in the following categories is provided:
Use Classification · 6 条

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

应用领域 · 5 条

应用乙酰丙酸的应用范围很广。乙酰丙酸即可作为羧酸又可作为酮发生反应，通过酯化、卤化、加氢、氧化脱氢、缩合等，制取各种产品，包括树脂、医药、香料、溶剂、涂料和油墨、橡胶和塑料助剂、润滑油添加剂、表面活性剂等。在医药工业中、其钙盐（果糖酸钙）可制静脉注射剂。作为营养药，有助于骨质的形成并维持神经和肌肉的正常兴奋性，还用于生产消炎痛、植物激素。乙酰丙酸制取的双酚酸可制造水溶性树脂，应用于造纸工业生产过滤纸。乙酰丙酸也是农药、染料的中间体。

用途用作医药、香料、涂料的原料，并用作溶剂

用途作为一种重要的化工原料或溶剂可用于生产医药（静脉注射剂、消炎痛等），树脂（双酚酸制水溶性树脂），香料（食用香料或烟草香料），油漆，涂料，农药，染料和表面活性剂等。

用途生化研究。制造酯类和药物。叶绿素合成的抑制剂。

用途用作生化试剂，也用于有机合成

制备方法 · 2 条

制备一种从单糖水解液中分离乙酰丙酸的方法，用离子交换树脂吸附法从单糖水解液中提取分离出高纯度乙酰丙酸的方法。技术方案是其步骤如下：以单糖水解液为起始原料，经柱层析分离、常压浓缩和减压精馏得到高含量的乙酰丙酸；整个分离过程如下：1)弱碱性阴离子交换树脂用湿法装柱，预处理后备用；将单糖水解液通过层析柱，流速为0.5～3.0倍床层体积/小时，温度为20～40℃；2)用去离子水冲洗层析柱，洗去单糖水解液中的中性杂质，流速为0.5～3.0 倍床层体积/小时，温度为20～40℃：3)用0.1～1.0mol/l的洗脱液将吸附在树脂上的乙酰丙酸洗脱下来，流速为 0.3～2.0倍床层体积/小时，温度为20～40℃；分部收集洗脱液，合并纯乙酰丙酸水溶液的流分，常压浓缩和0.01～0.05MPa下精馏即得高含量乙酰丙酸。

生产方法棉子壳或玉米芯制糖醛后的残渣（糠醛渣）或废山芋渣用稀酸加压水解可制得乙酰丙酸。将糖醛渣加入10%稀盐酸中，其固化液为1：1.75，混合均匀后投入水解锅，以0.2MPa压力的蒸汽蒸煮8－10h。然后将水解后的稀液过滤、浓缩至浓度50%左右。再进行减压精馏，收集130℃（2.67kPa）以上馏分即得成品。原料消耗定额：山芋渣打7000kg/t、盐酸（折100%）1800kg/t。另一种制法由糖醇经重排、水解而制得。将4%的盐酸溶液加入反应锅，搅拌加热至97-100℃，缓缓加入糠醇、乙醇、水的混合液。加毕，再搅拌30min。过滤，滤液于80℃（21.3kPa）减压浓缩，得粗品乙酰丙酸液。然后减压蒸馏，收集160-170℃（2.67kPa）馏分，再重新蒸馏一次，得精制乙酰丙酸，收率75%左右。

上下游产品信息

试剂价格

A10813 · 250g
乙酰丙酸, 98% Levulinic acid, 98% — 372元
12514 · 5kg
乙酰丙酸Levulinic Acid, 98+%, Thermo Scientific Chemicals — 4248元

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