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グルタル酸

Glutaric Acid

HCID 743
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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
110-94-1
標準SMILES
O=C(O)CCCC(=O)O
InChIKey
JFCQEDHGNNZCLN-UHFFFAOYSA-N
分子式
C5H8O4
平均分子量
132.11 g/mol
単同位体質量
132.04225874

概要

Glutaric acid appears as colorless crystals or white solid. (NTP, 1992)

名称と識別子

優先名称
Glutaric Acid
IUPAC
pentanedioic acid
現地名
グルタル酸
英語名
Glutaric acid
分子式
C5H8O4
分子量
132.11

名称と別名

GLUTARIC ACIDPentanedioic acid110-94-11,5-Pentanedioic acidglutarate1,3-Propanedicarboxylic acidPentandioic acidn-Pyrotartaric acidDTXSID2021654CHEBI:17859H849F7N00BNSC-9238
名称をさらに表示
グルタル酸グルタル酸 (約4.3mol/L 水溶液)n-ピロ酒石酸ペンタン二酸1,3-プロパンジカルボン酸グルタール酸グルタル酸 (約50%水溶液, 約4.3mol/L)1,3-プロパンジカルボン酸 (約50%水溶液, 約4.3mol/L)ペンタン二酸 (約50%水溶液, 約4.3mol/L)グルタル酸, 99%glutaricG1utaric Acid1,5-PENTADIOIC ACIDGlutarsureutaric acidGlutarsaurelutaric acid
DTXCID401654hydron;pentanedioateRefChem:5863CHEBI:24329203-817-2Pentanedioatepropane-1,3-dicarboxylic acidMFCD00004410

データベース識別子

CAS
110-94-1
PubChem CID
743
DTXSID
DTXSID2021654
ChEMBL
CHEMBL1162495
ChEBI
CHEBI:17859
UNII
H849F7N00B
EC Number
203-817-2
Nikkaji
J40.077G

物性

構造計算による物性

XLogP
-0.3
極性表面積
74.6 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
4
重原子数
9
形式電荷
0
複雑度
104

実験および物理化学的性質

Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsCosmetic ingredients (Glutaric Acid) -> CIR (Cosmetic Ingredient Review)
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
LogP · 3 件

-0.29

-0.47/-0.08 (calculated)

-0.29

Density · 3 件

1.424 at 77 °F (NTP, 1992) - Denser than water; will sink

1.429 @ 15 °C/4 °C

1.4 g/cm³

Flavoring AgentsEU Flavoring substances
Color/Form · 2 件

LARGE, MONOCLINIC PRISMS

COLORLESS CRYSTALS

Solubility · 5 件

greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)

SOLUBILITY IN WATER (G/L): @ 0 DEG: 429; @ 20 DEG: 639; @ 50 DEG: 957; @ 65 DEG: 1118; FREELY SOL IN ABSOLUTE ALCOHOL, ETHER; SOL IN BENZENE, CHLOROFORM; SLIGHTLY SOL IN PETROLEUM ETHER

SOL IN CONCENTRATED SULFURIC ACID

1600.0 mg/mL

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 · 5 件

This chemical does not meet GHS hazard criteria for 3.7% (13 of 350) of reports.

Danger

H314 (49.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P337+P317, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 350 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 5 件

Chemical: Pentanedioic acid

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Pentanedioic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pentanedioic acid 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: 16-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19290

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

Other Safety InformationIMAP assessments - Pentanedioic acid: Human health tier I assessment
Fire Hazards · 2 件

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Combustible.

Health HazardsSYMPTOMS: This compound may cause irritation to the skin and eyes.
Hazards SummaryA skin, eye, and respiratory tract irritant; [ICSC] May cause skin and eye irritation; [CAMEO] Causes diarrhea and weight loss in high-dose animal feeding studies; [RTECS] An eye irritant; [MSDSonline]

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

RAT LIVER MITOCHONDRIA METABOLIZED GLUTARATE VERY SLOWLY COMPARED WITH GLUTARYL-COENZYME A (COA). GLUTARYL-COA DEHYDROGENASE, WHICH CATALYZES THE STOICHIOMETRIC CONVERSION OF GLUTARYL-COA TO 1 MOLE EACH OF CARBON DIOXIDE AND CROTONYL-COA OR ITS INTERMEDIATE METABOLITE, WAS PURIFIED APPROX 44- AND 100-FOLD FROM BOVINE LIVER AND KIDNEY MITOCHONDRIA, RESPECTIVELY. THE KM FOR GLUTARYL-COA WAS 3.3 MUM.

Tissue LocationsPlacenta
Cellular LocationsCytoplasm

用途と製造

Uses · 6 件

CIR ingredient: Glutaric Acid

Present in green sugar beets and water extracts of crude wool; [Merck Index] Used to make polymers, for biochemical research, and to treat animal diabetes; [HSDB]

IN ORGANIC SYNTHESIS

CHEM INT FOR POLYMERS, EG, POLYAMIDES & POLYESTERS

CHEM INT FOR ITS ESTERS & ANHYDRIDE

MEDICATION

U.S. Exports · 2 件

(1979) No Data

(1981) No Data

U.S. Imports · 2 件

(1979) No Data

(1981) No Data

U.S. Production · 3 件

2023: 25,000,000 - <40,000,000 lb

(1977) AT LEAST 4.54X10+9 GRAMS

(1981) No Data

Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesIntermediate
Methods of Manufacturing · 2 件

MANUFACTURED FROM CYCLOPENTANONE BY OXIDATIVE RING FISSION WITH HOT 50% NITRIC ACID IN THE PRESENCE OF VANADIUM CYANIDE. LAB PREPN BY ACID HYDROLYSIS OF TRIMETHYLENE CYANIDE...OR OF METHYLENEDIMALONIC ESTER.

関連反応

80 件
反応記録を作成
HRID 9745 の反応式
HRID 9745生成物としてuspto-grants-2006_08
HRID 99453 の反応式
HRID 99453生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 159400 の反応式
HRID 159400反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 253934 の反応式
HRID 253934反応物としてuspto-grants-2011_01
HRID 430418 の反応式
HRID 430418反応物としてuspto-grants-2001_11
HRID 462907 の反応式
HRID 462907反応物としてuspto-grants-1985_05
HRID 462908 の反応式
HRID 462908反応物としてuspto-grants-1985_05
HRID 462909 の反応式
HRID 462909反応物としてuspto-grants-1985_05
1 / 10 ページ

化合物ノート

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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

Solubility in water, g/100ml at 20 °C: 63.9

Boiling Point · 3 件

576 to 579 °F at 760 mmHg (decomposes) (NTP, 1992)

200 °C @ 20 MM HG

303.00 °C. @ 760.00 mm Hg

Decomposition302-304 °C
Melting Point · 4 件

207.5 °F (NTP, 1992)

97.5-98 °C

95.8 °C

98 °C

物理化学的性質

融点
95 · 95-98 °C (lit.)
沸点
200 °C/20 · 200 °C/20 mmHg (lit.)
比重(密度)
1 · 1,429 g/cm3
蒸気圧
0.022 hPa · 0.022 hPa (18.5 °C)
屈折率
106 · nD106 1.41878
闪点
200 °C/20mm · 200°C/20mm
貯蔵温度
30 °C · Store below +30°C.
溶解性
5 mg/mL、透明～やや濁り、無色～微黄色 · 水：可溶5mg/mL、透明～やや濁り、無色～微黄色
酸解離定数(Pka)
4.31 · 4.31(at 25℃)
外見
結晶性粉末
色
オレンジ
PH
3.7 · 3.7(1 mM solution);3.17(10 mM solution);2.66(100 mM solution)
水溶解度
430 g/L · 430g/L(20℃)
Merck
14 · 14,4473
BRN
1209725 · 1209725
Henry's Law Constant
3.8 · 3.8×107 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
安定性
安定。塩基、酸化剤、還元剤と相容れない。
化粧品成分の機能
バッファリング
InChI
1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)
InChIKey
JFCQEDHGNNZCLN-UHFFFAOYSA-N
SMILES
OC(=O)CCCC(O)=O
LogP
-0.26 at · -0.26 at 25℃
CAS データベース
110 · 110-94-1(CAS DataBase Reference)
NISTの化学物質情報
Pentanedioic acid(110-94-1)
EPAの化学物質情報
Pentanedioic acid (110-94-1)

化学的性質

化学的特性white or off-white crystals, usually containing 1mol crystal water. Soluble in water, alcohol, ether and chloroform, slightly soluble in petroleum ether.

Reactive GroupAcids, Carboxylic
EPA Safer ChemicalChemical: Glutaric acid
Reactivity Profile · 1 件

GLUTARIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions This compound reacts with bases, oxidizing agents and reducing agents. (NTP, 1992)

Chemical DangersThe solution in water is a medium strong acid.
Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesSkin Corr. 1A (49.7%)

安全と保護具

Fire Fighting · 2 件

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)

Use water spray, powder.

First Aid Measures · 4 件

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

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.

Safe StorageSeparated from bases.
Exposure Control and Personal Protection2.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces 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.

Spillage DisposalSweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Then wash away with plenty of water.
Eye PreventionWear safety spectacles or safety goggles.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.

毒性情報

InteractionsLITHIUM CHLORIDE (1.15 G) OR LITHIUM CARBAMATE (1.5-4 G) INCREASED THE RENAL EXCRETION OF GLUTARATE IN MANIC DEPRESSIVE PATIENTS. THE EFFECTS OF LITHIUM ARE PROBABLY CAUSED BY DECREASED RENAL TUBULAR RESORPTION.
Health EffectsChronically high levels of glutaric acid are associated with at least 3 inborn errors of metabolism including: Glutaric Aciduria Type I and Glutaric Aciduria Type III.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol.
Toxicity Summary · 2 件

Safe 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

Accumulation of glutaric acid in the body has been shown to be toxic. The accumulation of glutaric acid ranging from slightly or intermittently elevated urinary glutaric acid to gross organic aciduria occurs in glutaric aciduria. Glutaric aciduria type 1 is an autosomal-recessive disorder resulting from a deficiency of mitochondrial glutaryl-CoA dehydrogenase which is involved in the metabolism of lysine, hydroxylysine, and tryptophan.

Signs and Symptoms · 4 件

Cough. Sore throat.

Redness. Pain.

Pain. Redness.

Abdominal pain.

Natural Pollution SourcesOCCURS IN GREEN SUGAR BEETS; IS FOUND IN WATER EXTRACTS OF CRUDE WOOL.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

wgk
1
tsca
TSCA listed
rtecs
MA3740000
hs_code
29171990
risk_code
36-36/37/38
化審法
(2)-2560
hazard_code
Xi
safety_code
26-37/39-36-39
Hazard Classifications
Eye Dam. 1Skin Corr. 1A
ストレージクラス
8A - Combustible corrosive hazardous materials
有毒物質データの
110-94-1(Hazardous Substances Data)
危険度評価（NFPA 704基準/消防庁データ）
人的[青]=0

OXIDATION OF CYCLOPENTANONE WITH 50% NITRIC ACID IN THE PRESENCE OF VANADIUM PENTOXIDE OR WITH AIR IN THE PRESENCE OF A CATALYST; BY-PRODUCT IN THE PRODUCTION OF ADIPIC ACID FROM CYCLOHEXANE BY OXIDATION WITH AIR & NITRIC ACID

Use Classification · 3 件

EPA Safer Chemical Functional Use Classes -> Processing Aids and Additives

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Environmental transformation -> Pesticide transformation products (metabolite, successor)

General Manufacturing Information · 5 件

Petroleum Lubricating Oil and Grease Manufacturing

Pentanedioic acid: ACTIVE

15,000 CU M/HR OFFGAS CONTAINING 10-15% SULFUR DIOXIDE & 0.5-2 MG H2S/CU M IS SCRUBBED IN 4 SUCCESSIVE PACKED COLUMNS @ 35 °C WITH 40-55 CU M/HR 30% AQ GLUTARIC ACID.

A COMPOSITION FOR NEUTRALIZING OR DESTROYING A SUSCEPTIBLE VIRUS ON INFECTED TISSUE OF A LIVING MAMMAL CONTAINS AN EFFECTIVE CONCN OF GLUTARIC ACID IN PHARMACEUTICAL VEHICLE AS WELL AS PAPER OR CLOTH COATED OR IMPREGNATED WITH THE VIRUCIDE.

GLUTARIC ACID MAY BE AN ESSENTIAL PRECURSOR IN THE BIOSYNTHESIS OF BIOTIN BY A SPECIES OF AGROBACTERIUM.

応用分野 · 7 件

解説pentanedioic acid．C5H8O4(132.11)．HOOC(CH2)3COOH．シクロペンタノールあるいはシクロペンタノンを酸化するか，グルタコン酸の水素付加で合成される．実験室的には，1,3-ジブロモプロパンにシアン化カリウムを作用させて，ジニトリルとして加水分解すると得られる．無色の板状結晶．グルタル酸, 融点97～98 ℃，沸点302～304 ℃，200 ℃(2.7 kPa)．水，エタノール，エーテルに易溶．種々の合成高分子用可塑剤の合成原料として用いられる．森北出版「化学辞典（第2版）

解説飽和の鎖式ジカルボン酸の一つ。1,3-プロパンジカルボン酸またはペンタン二酸ともいう。実験室的には1,3-ジブロモプロパンにシアン化ナトリウムを作用させてグルタロニトリルとし、それを加水分解することにより得られる。酢酸よりやや強い酸である。可塑剤の合成中間体として用いる。糖・脂肪などの代謝回路（TCA回路）に関与していて、生物学的にも重要である。

用途有機合成原料、ポリマー。

天然物の起源Glutaric acid occurs in washings from fleece and, together with malonic acid, in the juice of unripened sugar beet.

使用Glutaric acid is used as the raw material for organic synthesis, pharmaceutical intermediate and synthetic resin. It serves as a precursor in the production of polyester polyols, polyamides, ester plasticizers and corrosion inhibitors. It is useful to decrease polymer elasticity and in the synthesis surfactants and metal finishing compounds. It acts as an intermediate during the catabolism of lysine in mammals.

一般的な説明Glutaric acid appears as colorless crystals or white solid. (NTP, 1992)

使用用途グルタル酸は溶解性が高く残留物が少ないため、はんだフラックスの調整やはんだペーストの製造に使用されています。また、ポリエステルポリオール、ポリアミドなどの有機合成原料としても有用です。グルタル酸には、ポリマーの弾性を低下させる作用があります。 そのほか、医薬品の中間体や無水グルタル酸・l-ケトグルタル酸・ペルオキシグルタル酸などの開始剤、香料、pH調整剤としても利用されています。

調製方法 · 2 件

製造方法glutaric acid is produced as a by-product of the production process of adipic acid (about 2% of the output of an adipic acid plant is glutaric); Glutaric acid can be produced through various chemical routes, for example, from cyclopentane by oxidation with molecular oxygen and cobalt (III) catalysts or by ozonolysis; and from cyclopentanol–cyclopentanone by oxidation with oxygen and Co(CH3CO2)2, with potassium peroxide in benzene, or with N2O4 or nitric acid. Together with succinic acid, glutaric acid is formed as a by-product during oxidation of cyclohexanol–cyclohexanone in the adipic acid production process.

純化方法Crystallise the acid from *benzene, CHCl3, distilled water or *benzene containing 10% (w/w) of diethyl ether. Dry it under vacuum. [Beilstein 2 IV 1934.]

上流・下流製品情報

上流原料

アジピン酸oxidized paraffin(wax)パラフィンDihydropyran2,3-ジヒドロフラン四酸化二窒素1,3-プロパンジオールグルタロニトリル塩化アンモニウム硝酸シクロヘキサノンシクロペンタノンシアン化カリウムγ-ブチロラクトンδ-ホルミル吉草酸こはく酸シクロペンタノールシクロペンタン

下流製品

ブスピロンrac-2β*-(2-メチルベンジルオキシ)-4α*-イソプロピル-1α*-メチル-7-オキサビシクロ[2.2.1]ヘプタンアゼライン酸グルタル酸無水物バクロフェンラッカイン酸
補足説明 · 2 件

定義本品は、次の化学式で表される有機化合物である。

定義ChEBI: glutaric acid is an alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid. It has a role as a human metabolite and a Daphnia magna metabolite. It is an alpha,omega-dicarboxylic acid and a dicarboxylic fatty acid. It is a conjugate acid of a glutarate(1-) and a glutarate.