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프로판디알

Malonaldehyde

HCID 10964
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
542-78-9
표준 SMILES
O=CCC=O
InChIKey
WSMYVTOQOOLQHP-UHFFFAOYSA-N
분자식
OCHCH2CHO
평균 분자량
72.06 g/mol
단동위원소 질량
72.02112937

개요

Malonaldehyde is a dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form. It has a role as a biomarker.

이름 및 식별자

우선 이름
Malonaldehyde
IUPAC
propanedial
현지명
프로판디알
영어명
propanedial
분자식
C3H4O2
분자량
72.06

이름 및 동의어

PropanedialMALONALDEHYDEMalondialdehyde542-78-9MalonodialdehydeMalonic aldehydeMalonyldialdehydeMalonic dialdehyde1,3-Propanedial1,3-Propanedione1,3-PropanedialdehydeNCI-C54842
이름 더 보기
프로판디알Malonaldehyde.3-OxopropanalmalondialchehychePropanedial (9CI)Malonyl dialdehydeSelamectin Impurity 6Propanedial Standard Solution
CHEBI:5662744Y8F71G49QDTXSID90202556MalonylaldehydemalonicdialdehydeMalondialdehyde, SodiumRefChem:155442DTXCID20125047

데이터베이스 식별자

CAS
542-78-9
PubChem CID
10964
DTXSID
DTXSID90202556
ChEMBL
CHEMBL446036
ChEBI
CHEBI:566274
UNII
4Y8F71G49Q
Nikkaji
J1.601B

물성

구조 계산 물성

XLogP
-0.6
극성 표면적
34.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
2
무거운 원자 수
5
형식 전하
0
복잡도
34.2

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Aldehydes
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCoriolis coupling
LogP-1.16
Color/FormSolid (needles)
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point · 3건

72 °C

72 °C

161 °F

Physical Description · 4건

Solid (needles); [NIOSH]

Solid

NEEDLES.

Solid (needles).

물리화학적 성질

녹는점
72 · 72-74°
끓는 점
66.43 °C · 66.43°C (rough estimate)
밀도
0.9843 · 0.9843 (rough estimate)
굴절률
1.367 · 1.3670 (estimate)
용해도
2 O; · sol EtOH, MeOH, H2O; moderately sol CH2Cl2; insol ether.
산도 계수 (pKa)
5 · 5(at 25℃)
Henry's Law Constant
7.3 · 7.3×101 mol/(m3Pa) at 25℃, Wang et al. (2017)
InChI
InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2
InChIKey
WSMYVTOQOOLQHP-UHFFFAOYSA-N
SMILES
C(=O)CC=O
LogP
-0.39 · -0.390 (est)

안전 및 규제

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

유해성 정보

Fire HazardsNot combustible.
Hazards Summary · 1건

Evidence of injury to the liver and pancreas in mice experiments when added to drinking water at 500 mg/kg body weight per day; [HSDB] No listed effects of short-term or long-term exposure; [ICSC] May cause skin, eye, and respiratory tract irritation; Excessive exposure may cause CNS depression; [Merck Index] Causes muscle weakness, dyspnea, and cyanosis in oral lethal-dose study of rats; Causes other gastrointestinal and liver changes and inflammation, necrosis, or scarring of bladder in 90-day oral study of mice; [RTECS] See ALDEHYDES

Special Reports · 1건

DHHS/NTP; Toxicology & Carcinogenesis Studies of Malonaldehyde, Sodium Salt (3-Hydroxy-2-propenal, sodium salt) in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 331 (1988) NIH Publication No. 88-1792 /Malonaldehyde, sodium salt/

Chemical DangersDecomposes on heating. This produces toxic fumes.
NIOSH Recommendations · 2건

NIOSH considers maloaldehyde to be a potential occupational carcinogen.

NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.

Hazardous Reactivities and Incompatibilities · 2건

Proteins [Note: Pure compound is stable under neutral conditions, but not under acidic conditions].

Proteins [Note: Pure compound is stable under neutral conditions, but not under acidic conditions.]

안전 및 보호

Fire FightingIn case of fire in the surroundings, use appropriate extinguishing media.
First Aid Measures · 4건

Fresh air, rest. Refer for medical attention.

Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink.

First Aid(General first aid procedures)
Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1건

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 5건

The worker should immediately wash the skin when it becomes contaminated.

The worker should wash daily at the end of each work shift.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

For more Preventive Measures (Complete) data for MALONALDEHYDE (6 total), please visit the HSDB record page.

Eye PreventionWear safety goggles.
Inhalation RiskA harmful concentration of airborne particles can be reached quickly.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse ventilation, local exhaust or breathing protection.
Respirator RecommendationsNIOSH

독성 정보

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Cancer Sites[in animals: thyroid gland tumors]
Target OrgansEyes, skin, respiratory system, central nervous system
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Food Survey Values · 1건

MALONALDEHYDE IS FOUND IN MANY FOODSTUFFS AND IS PRESENT AT GENERALLY HIGH LEVELS IN RANCID FOODS. IT HAS BEEN DETECTED IN FISH MEAT, FISH OIL, RANCID SALMON OIL, RANCID NUTS, RANCID FLOUR, ORANGE JUICE ESSENCE, VEGETABLE OIL, FATS, FRESH FROZEN GREEN BEANS, MILK, MILK FAT, RYE BREAD, AND IN RAW, CURED AND COOKED MEATS.

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure Routes · 3건

The substance can be absorbed into the body by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Endogenous, Ingestion, Dermal (contact)

Toxicity Summary · 1건

Uremic toxins such as malondialdehyde are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).

Plant ConcentrationsMALONALDEHYDE HAS BEEN DETECTED IN THE LEAVES OF PEA AND COTTON PLANTS.

안전 데이터

독성
LD50 orally in rats: 632 mg/kg (Crawford)
유해 물질 데이터
542-78-9(Hazardous Substances Data)

화학 및 산업

약리 정보

Metabolism/Metabolites · 5건

THIOBARBITURIC ACID-REACTING MATERIAL PRODUCED DURING ENZYMIC MICROSOMAL LIPID PEROXIDATION WAS IDENTIFIED AS MALONALDEHYDE. PHOSPHOLIPID ARACHIDONATE WAS ESTABLISHED AS THE MAJOR SOURCE OF THE MALONALDEHYDE PRODUCED IN THE REACTION.

(14)C-ACETATE APPEARED TO BE THE MAJOR ACCUMULATING METABOLITE IN RAT LIVER MITOCHONDRIAL PREPARATIONS FOLLOWING A 120-MINUTE INCUBATION WITH (14)C-MALONALDEHYDE. A PROBABLE BIOCHEMICAL ROUTE FOR MALONALDEHYDE METABOLISM INVOLVES OXIDATION OF MALONALDEHYDE BY MITOCHONDRIAL ALDEHYDE DEHYDROGENASE FOLLOWED BY DECARBOXYLATION TO PRODUCE CARBON DIOXIDE AND ACETATE.

Two aldehyde dehydrogenases in the rat-liver cytosol fraction account for virtually all of the metabolizing activity for malonaldehyde.

After oral administration of malonaldehyde (158 mg/kg body weight) to rats, increased quantities of formaldehyde, acetaldehyde, acetone and malonaldehyde itself were found in the urine. Additionally, methyl ethyl ketone, not found in control rats, was present in the urine of the animals that had received malonaldehyde.

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

Absorption, Distribution and Excretion · 2건

IN PRIMARY RAT SKIN FIBROBLAST CULTURES GROWN IN A MEDIUM CONTAINING 1X10(-5), 1X10(-4), OR 1X10(-3) MOLAR OF 1,3-(14)C MALONALDEHYDE, THERE WAS A LIMITED, CONCENTRATION-DEPENDENT UPTAKE OF MALONALDEHYDE BY 24 HR (APPROXIMATELY 4% AT ALL CONCENTRATIONS). 83-89% OF THE (14)C WAS OXIDIZED TO (14)CO2 BY 24 HR AND APPROXIMATELY 5% WAS RECOVERED IN THE MAJOR LIPIDS. LIMITED CELLULAR UPTAKE OF MALONALDEHYDE MAY EXPLAIN THE TOLERANCE OF CELLS GROWN IN CULTURE TO RELATIVELY HIGH CONCENTRATIONS.

TWELVE HOURS AFTER INTUBATION WITH 1,3-(14)C MALONALDEHYDE, MALE WISTAR RATS SHOWED 60-70%, 5-15% AND 9-17% OF ADMINISTERED RADIOACTIVITY IN EXPIRED CARBON DIOXIDE, FECES AND URINE, RESPECTIVELY. IN VITRO EXPERIMENTS SHOWED METABOLISM TO BE PRIMARILY IN MITOCHONDRIA VIA REACTIONS INVOLVING OXYGEN UTILIZATION AND (14)CO2 PRODUCTION. THE APPARENT KM AND VMAX WERE 0.5 MMOL AND 9.3 NMOL/MIN/MG PROTEIN FOR OXYGEN UPTAKE, RESPECTIVELY, AND 2.0 MMOL AND 2.4 NMOL/MIN/MG PROTEIN FOR (14)CO2 PRODUCTION.

용도 및 제조

Uses · 3건

Used in scientific research; [HSDB] Produced during lipid peroxidation and other reactions in mammals; Used as index for rancidity in foods; [Merck Index] Found in many foods (at high levels if rancid); [IARC]

RESEARCH COMPOUND

Naturally produced by the body (endogenous).

U.S. Exports(1986) No Data
U.S. Imports(1986) No Data
U.S. ProductionNO COMMERCIAL PRODUCTION
Methods of ManufacturingFREE MALONALDEHYDE CAN BE GENERATED FROM/ITS BIS(DIALKYL)ACETALS (eg 1,1,3,3-TETRAETHOXYPROPANE)/BY ACID-CATALYZED HYDROLYSIS WITH DILUTE HYDROCHLORIC ACID OR SHAKING THEM WITH ACID DOWEX 50 ION-EXCHANGE RESIN

응용 분야

용도Propanedial, exists in horseradish hairy root taht has shown strong antioxidant capacity under arsenic stress which indicates possible use of Armoracia rusticana plants for phytoremediation.

상·하류 제품 정보

상류 원료

3-아미노프로판알1,3-디아미노프로판

공급사31 곳

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추가 설명 · 1건

정의Malonaldehyde is a dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form. It has a role as a biomarker.

관련 반응

3건
반응 기록 만들기
HRID 1031273 반응식
HRID 1031273반응물로uspto-grants-1992_04
HRID 2165465 반응식
HRID 2165465반응물로uspto-grants-1990_07
HRID 2229804 반응식
HRID 2229804반응물로uspto-grants-2002_07

화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Signs and Symptoms · 4건

Cough.

Redness.

irritation eyes, skin, respiratory system; central nervous system depression; [potential occupational carcinogen]

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Ongoing Test Status · 1건

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. /Malonaldehyde, sodium salt/ [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=24382-04-5]

Natural Pollution Sources · 1건

MALONALDEHYDE HAS BEEN DETECTED IN LIPID-PEROXIDIZING MICROSOMES AND IS FOUND IN ANIMAL TISSUE AS AN END-PRODUCT OF LIPID PEROXIDATION. IT IS ALSO A SIDE-PRODUCT OF PROSTAGLANDIN AND THROMBOXANE BIOSYNTHESIS. MALONALDEHYDE HAS BEEN DETECTED IN THE LEAVES OF PEA AND COTTON PLANTS.

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