홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /화합물

카다베린

Cadaverine

HCID 273
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
462-94-2
표준 SMILES
NCCCCCN
InChIKey
VHRGRCVQAFMJIZ-UHFFFAOYSA-N
분자식
C5H14N2
평균 분자량
102.18 g/mol
단동위원소 질량
102.11569846

개요

Cadaverine is an alkane-alpha,-diamine comprising a straight-chain pentane core with amino substitutents at positions 1 and 5. A colourless syrupy liquid diamine with a distinctive unpleasant odour, it is a homologue of putresceine and is formed by the bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. It is also found in plants such as soyabean. It has a role as a mouse metabolite, a plant metabolite, an Escherichia coli metabolite and a Daphnia magna metabolite. It is a conjugate base of a cadaverine(2+).

이름 및 식별자

우선 이름
Cadaverine
IUPAC
pentane-1,5-diamine
현지명
카다베린
영어명
1,5-Diaminopentane
분자식
C5H14N2
분자량
102.18

이름 및 동의어

Pentane-1,5-diamine1,5-Diaminopentanecadaverine462-94-21,5-pentanediaminepentamethylenediamineCadaverin1,5-PentamethylenediamineAnimal coniine1,5-Diamino-n-pentaneL90BEN6OLLDTXSID5075448
이름 더 보기
디아미노펜탄(1,5-)카다베린펜타메틸렌다이아민PDAPDAPDAPDA1,4-Pentanediamine
CHEBI:181271,5 PentanediamineRefChem:5628DTXCID9040479207-329-0AI3-26937BRN 1697256pentane, 1,5-diamino-

데이터베이스 식별자

CAS
462-94-2
PubChem CID
273
DTXSID
DTXSID5075448
ChEMBL
CHEMBL119296
ChEBI
CHEBI:18127
UNII
L90BEN6OLL
EC Number
207-329-0
Nikkaji
J5.771A

물성

구조 계산 물성

XLogP
-0.6
극성 표면적
52 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
2
회전 가능 결합 수
4
무거운 원자 수
7
형식 전하
0
복잡도
25.3

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Amines, Aliphatic
DrugsPharmaceuticals -> Listed in ZINC15
pHStrong base
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Odor · 2건

Characeteristic odor

... partially responsible for the distinctive smell of urine and semen

Density0.873 g/cu cm at 25 °C
Color/Form · 2건

Syrupy, colorless liquid

Thick fuming liquid

SolubilitySoluble in water, ethanol; slightly soluble in ethyl ether
Flash Point62 °C (144 °F) - closed cup
Boiling Point179 °C
DecompositionWhen heated to decomposition it emits highly toxic fumes of /nitroxides/.
Melting Point

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Danger

H302+H312 (64.2%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 162 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 5건

Chemical: 1,5-Pentanediamine

1,5-Pentanediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,5-Pentanediamine 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)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

REACH registered substance: Pentamethylenediamine (EC: 207-329-0)

1,5-Pentanediamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Fire PotentialCombustible liquid
Hazards Summary · 1건

A strong base that attracts carbon dioxide; A skin irritant and possible sensitizer; [Merck Index] Causes burns; [HSDB] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS] Search for (462-94-2[EC/RN Number]) AND (sensitizer OR sensitization OR allergic OR dermatitis): no papers confirming skin sensitization; [PubMed] See 1,6-Diaminohexane.

화학 및 산업

약리 정보

Metabolism/Metabolites · 3건

It is a precursor of piperidine, which has been linked with some functional stages of the CNS. Cadaverine is the source of much of the piperidine excreted in the urine.

Cadaverine ... a relatively nontoxic ptomaine, C5H14N2, formed by decarboxylation of lysine; it is sometimes one of the products of Vibrio proteus and of V. cholerae, and occasionally found in the urine in cystinuria, where it causes an unpleasant odor.

Cadaverine is synthesized from lysine in a one-step reaction with lysine decarboxylase (LDC).

Absorption, Distribution and Excretion · 2건

The urinary excretion of histamine, methylhistamine, putrescine, cadaverine, spermidine and spermine was examined before, during and after pregnancy in rats. During the last third of undisturbed pregnancy a distinct and steep rise occurred in the excretion of all amines studied except spermine. The peak values were found a few days before the birth of the young. In spermidine excretion a second peak was observed one or two days after delivery. Before and during the first 2 weeks of gestation on a molar basis putrescine excretion was the greatest one. During the last trimester histamine was excreted in the largest amount. Under the influence of the diamine oxidase inhibitor aminoguanidine the general pattern of excretion of diamines and polyamines in pregnant rats remained essentially unchanged but the total amount excreted increased. Most conspicuous was the great elevation of urinary contents of putrescine and cadaverine.

Cadaverine has been shown to be present in the central nervous system (CNS) ... Its concentration in the whole brain varies during behavioral sleep in mammals and during hibernation in molluscs. ... Cadaverine has been considered a non-metabolite of the brain, and its presence in the body was believed to be due almost entirely to bacterial decarboxylation of lysine in the intestine. In slices of mouse brain, exogenous cadaverine accumulates against a concentration gradient and can reach a concentration ten times greater in the tissue than in the surrounding medium. The question has been therefore: does the cadaverine in the brain originate from an exogenous source; is it formed and resorbed in the intestine? Assaying cadaverine in axenic mice, /it has been/ found that this is not the case, and that there is an endogenous source of cadaverine in the mouse.

Tissue Locations

관련 반응

47건
반응 기록 만들기
HRID 26725 반응식
HRID 26725반응물로uspto-grants-1979_04
HRID 34752 반응식
HRID 34752반응물로uspto-grants-1988_08
HRID 50611 반응식
HRID 50611반응물로uspto-grants-2004_03
HRID 72840 반응식
HRID 72840반응물로uspto-grants-2014_09
HRID 144760 반응식
HRID 144760반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 304425 반응식
HRID 304425반응물로Training data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 353818 반응식
HRID 353818반응물로uspto-grants-2004_06
HRID 400342 반응식
HRID 400342반응물로uspto-grants-2014_06
1 / 6 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
· 2건

11.83 °C

9 °C

물리화학적 성질

녹는점
9 °C · 9 °C
끓는 점
178 · 178-180 °C(lit.)
밀도
0.873 g/mL · 0.873 g/mL at 25 °C(lit.)
증기압
1.29 · 1.29-17hPa at 20-25℃
굴절률
20 · n20/D 1.458(lit.)
인화점
145 °F · 145 °F
용해도
1 M · 1 M HCl: 용해성0.5g/10 mL, 투명, 무색
물리적 상태
액체
산도 계수 (pKa)
10.05 · 10.05(at 25℃)
색상
무색~황색으로 투명함
냄새
특유의 냄새
수용성
녹는
Merck
14 · 14,1609
BRN
1697256 · 1697256
안정성
안정적인. 산 염화물, 산, 산 무수물, 강산화제, 이산화탄소와 호환되지 않습니다.
InChI
1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
InChIKey
VHRGRCVQAFMJIZ-UHFFFAOYSA-N
SMILES
NCCCCCN
LogP
-0.3 · -0.3--0.15 at 21℃
NIST
1 · 1,5-Diaminopentane(462-94-2)
EPA
Cadaverine (462-94-2)

화학적 성질

colourless to light yellow liquid with a very unpleasant smell

NFPA Hazard Classification · 3건

3 - Materials that, under emergency conditions, can cause serious or permanent injury.

2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.

0 - Materials that in themselves are normally stable, even under fire conditions.

Toxic Combustion ProductsHazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx)
Hazard Classes and CategoriesAcute Tox. 4 (68.5%)
Skin, Eye, and Respiratory IrritationsAn irritant ...
Hazardous Reactivities and IncompatibilitiesMaterials to avoid Acid chlorides, Acid anhydrides, acids, Strong oxidizing agents, Carbon dioxide (CO2)

안전 및 보호

Fire Fighting ProceduresUse water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self contained breathing apparatus for fire fighting if necessary.
Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Store under inert gas.
Cleanup MethodsSoak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal. Do not let product enter drains.
Disposal Methods · 1건

This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: dispose of as unused product.

Preventive Measures · 5건

Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Personal Protective Equipment (PPE) · 2건

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Hand protection: Handle with gloves. Eye protection: Safety glasses Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.

Safety glasses, good ventilation, gloves

독성 정보

Interactions · 1건

Histamine poisoning can result from the ingestion of food containing unusually high levels of histamine. ... Histamine poisoning is characterized by a short incubation period, a short duration, and symptoms resembling those associated with allergic reactions. The evidence supporting the role of histamine as the causative agent is compelling. ... Histamine ingested with spoiled fish appears to be much more toxic than histamine ingested in an aqueous solution. The presence of potentiators of histamine toxicity in the spoiled fish may account for this difference in toxicity. Several potentiators including other putrefactive amines such as putrescine and cadaverine have been identified. Pharmacologic potentiators may also exist; aminoguanidine and isoniazid are examples. The mechanism of action of these potentiators appears to be the inhibition of intestinal histamine-metabolizing enzymes. This enzyme inhibition causes a decrease in histamine detoxification in the intestinal mucosa and results in increased intestinal uptake and urinary excretion of unmetabolized histamine.

Ecotoxicity ValuesLD50; Species: Peromyscus maniculatus (Deer Mouse) oral 1600 mg/kg
Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that cadaverine is expected to have high mobility in soil(SRC). However, the pKa values of cadaverine are 9.13 and 10.25(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as a cation and cations do not volatilize. Cadaverine is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data in soil were not available(SRC, 2010).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that cadaverine is not expected to adsorb to suspended solids and sediment(SRC). The pKa values of 9.13 and 10.25(3) indicate cadaverine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -0.15(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2010).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cadaverine, which has a /an estimated vapor pressure of 1.0 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cadaverine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6 hours(SRC), calculated from its rate constant of 6.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Cadaverine does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1건

Cadaverine levels in fresh pork and beef meat were not detected to 0.7 mg/kg and not detected, respectively. Levels in cooked ham and mortadella were not detected to 0.9 mg/kg and not detected to 7.9 mg/kg, respectively. The cadaverine content in ripened meat products ranged from 3.9 to 34.9 mg/kg chorizo and 2.1 to 68.5 mg/kg in salchichon(1).

Adverse EffectsDermatotoxin - Skin burns.
Toxicity Summary · 1건

IDENTIFICATION AND USE: Cadaverine is a syrupy, colorless liquid with a distinctive odor of urine and semen. It is soluble in water, ethanol; slightly soluble in ethyl ether, and miscible in water. It is used in the production of high polymers, as a chemical intermediate, and in biological research. HUMAN EXPOSURE AND TOXICITY: It is a foul-smelling diamine formed by bacterial decarboxylation of lysine. It is poisonous and irritating to the skin. Harmful if ingested, inhaled, or absorbed through the skin. It can cause burns and is very destructive of mucous membranes. Occupational exposure to cadaverine may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. Monitoring data indicate that the general population may be exposed to cadaverine by ingestion of certain meats. ANIMAL STUDIES: In In rats, cadaverine had a low oral toxicity. Cadaverine caused a dose-related decrease in blood pressure after intravenous administration in rats. The subacute toxicity of this chemical was examined in rats. Cadaverine was administered in the diet to groups of 10 male and 10 female rats. Adverse effects were observed in the high dose group and decreased body weights associated with diminished food intake were observed. Slight increases in packed cell volume, hemoglobin concentration, and thrombocytes occurred with chemical exposure.

Plant ConcentrationsCadaverine was detected, not quantified in unspecified freshwater and marine algae(1).
Effluent ConcentrationsCadaverine was tested for but not detected in gasoline nor diesel exhaust(1).
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of cadaverine can be estimated to be 90(SRC). According to a classification scheme(2), this estimated Koc value suggests that cadaverine is expected to have high mobility in soil. However, the pKa values of cadaverine are 9.13 and 10.25(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

Natural Pollution Sources · 1건

Cadaverine is a ptomaine formed in the decay of animal proteins after death(1). It is also produced in small quantities by living beings and is partially responsible for the distinctive smell of urine and semen(2). It is related to putrescine. Both are produced by the breakdown of amino acids in living and dead organisms(3).

Human Toxicity Excerpts · 2건

/SIGNS AND SYMPTOMS/ Cadaverine ... a foul-smelling diamine formed by bacterial decarboxylation of lysine. It is poisonous and irritating to the skin.

/SIGNS AND SYMPTOMS/ Stench! Harmful if ingested, inhaled, or absorbed through the skin. Corrosive - causes burns. Very destructive of mucous membranes.

Artificial Pollution SourcesCadaverine's production and use as a chemical intermediate and in biological research(1) may result in its release to the environment through various waste streams(SRC).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
SA0200000
ridadr
UN 2735 8/PG 3
독성
dni-mus:ast 10 mmol/L AMOKAG 33,149,79
HS 번호
29212900
risk_code
34-36/37
hazard_code
C
safety_code
26-36/37/39-45-25-27
포장분류
III
위험 등급
8
기존화학 물질
KE-27950
F 고인화성물질
10
Hazard Classifications
Eye Dam. 1Skin Corr. 1B
스토리지 클래스
8A - Combustible corrosive hazardous materials
유해 물질 데이터
462-94-2(Hazardous Substances Data)
Epidermis
Cellular LocationsCytoplasm

용도 및 제조

Uses · 2건

A foul-smelling diamine formed by bacterial decarboxylation of lysine. [ChemIDplus] Biogenic polyamine present in cholera discharge; [Merck Index] Formed from decay of animal proteins; Used to make high polymers, as an intermediate, and in biological research; [HSDB]

Preparation of high polymers, intermediate, biological research.

U.S. Production2023: <75,000 lb
Industry UsesIntermediate
Methods of Manufacturing... 1,5-Diaminopentane can be produced from/ the starting materials 1,5-dichloropentane (obtainable from tetrahydropyran), glutarodinitrile, or glutaraldehyde (e.g., Relugan, BASF).
General Manufacturing Information · 6건

Asphalt Paving, Roofing, and Coating Materials Manufacturing

1,5-Pentanediamine: ACTIVE

A ptomaine formed in the decay of animal proteins after death

... also made synthetically

Biogenic amines are non-volatile amines formed by decarboxylation of amino acids. Although many biogenic amines have been found in fish, only histamine, cadaverine, and putrescine have been found to be significant in fish safety and quality determination. Despite a widely reported association between histamine and scombroid food poisoning, histamine alone appears to be insufficient to cause food toxicity. Putrescine and cadaverine have been suggested to potentiate histamine toxicity. With respect to spoilage on the other hand, only cadaverine has been found to be a useful index of the initial stage of fish decomposition ...

Cadaverine - A syrupy, colorless, fuming ptomaine formed by the carboxylation of lysine by bacteria in decaying animal flesh.

응용 분야 · 2건

용도1,5-Diaminopentane is mainly used in organic synthesis.

일반 설명Cadaverine, a biogenic amine, belongs to the class of aliphatic diamines and is commonly found in food products including cheese, fish products, fermented sausages, fish sauces, etc. It can be used as a freshness marker and as an indicator of microbial spoilage since it is most commonly identified in food products as a result of inappropriate storage conditions and microbial contamination.

제조 방법 · 1건

생산 방법1,5-Diaminopentane can be prepared by methods similar to those described for 1,4-diaminobutane. The starting materials are 1,5-dichloropentane (obtainable from tetrahydropyran), glutarodinitrile, or glutaraldehyde. The compound is hygroscopic and has a very bad odor.

상·하류 제품 정보

상류 원료

L-리신Glutaronitrile

하류 제품

5-(디에틸아미노)펜틸아민Carbamic acid, N,N'-1,5-pentanediylbis-, C,C'-bis(1,1-dimethylethyl) esterN'-methylpentane-1,5-diamineN-Boc-카다베린2-N-(5-아미노펜틸)-아미노-5-브로모피리딘1,5-DiisothiocyanatopentaneCarbaMicacid,[5-(2,5-디히드로-2,5-디옥소-1H-피롤-1-일)펜틸]-,1,1-디메틸에틸에스테르
추가 설명 · 1건

정의ChEBI: An alkane-alpha,omega-diamine comprising a straight-chain pentane core with amino substitutents at positions 1 and 5. A colourless syrupy liquid diamine with a distinctive unpleasant odour, it is a homologue of putresceine and is formed by the bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. It is also found in plants such as soyabean.