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글루타르산

Glutaric Acid

HCID 743
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인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
110-94-1
표준 SMILES
O=C(O)CCCC(=O)O
InChIKey
JFCQEDHGNNZCLN-UHFFFAOYSA-N
분자식
C5H8O4
평균 분자량
132.11 g/mol
단동위원소 질량
132.04225874

개요

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

이름 및 식별자

우선 이름
Glutaric Acid
IUPAC
pentanedioic acid
현지명
글루타르산
영어명
Glutaric acid
분자식
C5H8O4
분자량
132.11

이름 및 동의어

GLUTARIC ACIDPentanedioic acid110-94-11,5-Pentanedioic acidglutarate1,3-Propanedicarboxylic acidPentandioic acidn-Pyrotartaric acidDTXSID2021654CHEBI:17859H849F7N00BNSC-9238
이름 더 보기
글루타르산글루타릭애씨드glutaricG1utaric Acid1,5-PENTADIOIC ACIDGlutarsureutaric acidGlutarsaurelutaric acid
DTXCID401654hydron;pentanedioateRefChem:5863CHEBI:24329203-817-2Pentanedioatepropane-1,3-dicarboxylic acidMFCD00004410

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
-0.3
극성 표면적
74.6 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
4
회전 가능 결합 수
4
무거운 원자 수
9
형식 전하
0
복잡도
104

실험 및 물리화학적 성질

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 · 3건

-0.29

-0.47/-0.08 (calculated)

-0.29

Density · 3건

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 · 2건

LARGE, MONOCLINIC PRISMS

COLORLESS CRYSTALS

Solubility · 5건

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

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 5건

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 · 2건

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]

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

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

용도 및 제조

Uses · 6건

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 · 2건

(1979) No Data

(1981) No Data

U.S. Imports · 2건

(1979) No Data

(1981) No Data

U.S. Production · 3건

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 · 2건

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.

관련 반응

80건
반응 기록 만들기
HRID 9745 반응식
HRID 9745생성물로uspto-grants-2006_08
HRID 99453 반응식
HRID 99453생성물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 159400 반응식
HRID 159400반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 253934 반응식
HRID 253934반응물로uspto-grants-2011_01
HRID 430418 반응식
HRID 430418반응물로uspto-grants-2001_11
HRID 462907 반응식
HRID 462907반응물로uspto-grants-1985_05
HRID 462908 반응식
HRID 462908반응물로uspto-grants-1985_05
HRID 462909 반응식
HRID 462909반응물로uspto-grants-1985_05
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Solubility in water, g/100ml at 20 °C: 63.9

Boiling Point · 3건

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 · 4건

207.5 °F (NTP, 1992)

97.5-98 °C

95.8 °C

98 °C

물리화학적 성질

녹는점
95 · 95-98 °C (lit.)
끓는 점
200 °C/20 · 200 °C/20 mmHg (lit.)
밀도
1 · 1,429 g/cm3
증기압
0.022 hPa · 0.022 hPa (18.5 °C)
굴절률
106 · nD106 1.41878
인화점
200 °C/20mm · 200°C/20mm
저장 조건
30 °C · Store below +30°C.
용해도
5 mg/mL, · 물: 용해성 5mg/mL, 투명하거나 약간 흐릿함, 무색 내지 희미한 노란색
산도 계수 (pKa)
4.31 · 4.31(at 25℃)
물리적 상태
결정성 분말
색상
오렌지 레드
수소이온지수(pH)
3.7 · 3.7(1 mM solution);3.17(10 mM solution);2.66(100 mM solution)
수용성
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)
안정성
안정적인. 염기, 산화제, 환원제와 호환되지 않습니다.
화장품 원료 기능
버퍼링
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℃
NIST
Pentanedioic acid(110-94-1)
EPA
Pentanedioic acid (110-94-1)

화학적 성질

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 · 1건

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%)

안전 및 보호

Fire Fighting · 2건

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 · 4건

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 · 1건

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 · 1건

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.

독성 정보

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 · 2건

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 · 4건

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).

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
MA3740000
HS 번호
29171990
risk_code
36-36/37/38
hazard_code
Xi
safety_code
26-37/39-36-39
기존화학 물질
KE-27970
Hazard Classifications
Eye Dam. 1Skin Corr. 1A
스토리지 클래스
8A - Combustible corrosive hazardous materials
유해 물질 데이터
110-94-1(Hazardous Substances Data)

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 · 3건

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 · 5건

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.

응용 분야 · 3건

출처Glutaric acid occurs in washings from fleece and, together with malonic acid, in the juice of unripened sugar beet.

용도Glutaric 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.

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

제조 방법 · 1건

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.

상·하류 제품 정보

상류 원료

아디핀산oxidized paraffin(wax)파라핀 왁스Dihydropyran디하이드로퓨란(2,3-)질소 테트라산화물1,3-프로판디올Glutaronitrile염화 암모늄질산사이클로헥사논사이클로펜타논사이안화 칼륨뷰티로락톤6-옥소헥산산숙신산사이클로펜타놀시클로펜탄

하류 제품

Buspirone신메틸린노난디 산글루타릭 안하이드라이드바클로펜내추럴적색25호
추가 설명 · 1건

정의ChEBI: 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.