化工社化工社 化学情報印刷レポート · 研究参考用
1,5-ジアミノペンタン
1,5-ジアミノペンタン · カダベリン · 1,5-ペンタンジアミン · 1,5-ペンタジアミン · ペンタン-1,5-ジアミン · ペンタメチレンジアミン · (ペンタン-1,5-ジイル)ジアミン · PDA
識別子と物理属性
| CAS No. | 462-94-2 |
|---|---|
| 分子式 | C5H14N2 |
| 平均分子量 | 102.18 g/mol |
| 単同位体質量 | 102.11569846 g/mol |
| SMILES | NCCCCCN |
| InChIKey | VHRGRCVQAFMJIZ-UHFFFAOYSA-N |
| PubChem CID | 273 |
| ChEMBL | CHEMBL119296 |
| ChEBI | CHEBI:18127 |
| EC No. | 207-329-0 |
| DTXSID | DTXSID5075448 |
| 現地名 | 1,5-ジアミノペンタン |
化学・物理的性質
| XLogP | -0.6 |
|---|---|
| 極性表面積 | 52 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 4 |
| 重原子数 | 7 |
| 形式電荷 | 0 |
| 複雑度 | 25 |
| pH | Strong base |
| 臭い | Characeteristic odor... partially responsible for the distinctive smell of urine and semen特有の臭い |
| 密度 | 0.873 g/cu cm at 25 °C0.873 g/mL at 25 °C(lit.) |
| Color/Form | Syrupy, colorless liquidThick fuming liquid |
| 溶解度 | Soluble in water, ethanolslightly soluble in ethyl etherM HCl: 可溶0.5g/10 mL、透明、無色溶ける |
| 引火点 | 62 °C (144 °F) - closed cup145 °F |
| 沸点 | 179 °C178-180 °C(lit.) |
| Decomposition | When heated to decomposition it emits highly toxic fumes of /nitroxides/. |
| 融点 | 11.83 °C9 °C |
| 蒸気圧 | 1.01 [mmHg]1.29-17hPa at 20-25℃ |
| 屈折率 | Index of refraction = 1.463 at 20 °C/Dn20/D 1.458(lit.) |
| Physical Description | CBIColorless syrupy liquid that fumes in airmp = 9 deg C[Merck Index] Colorless hygroscopic liquid with an amine-like odor[Alfa Aesar MSDS] |
| 外観・状態 | 液体 |
| pKa（酸解離定数） | 10.05(at 25℃) |
| 色 | 無色透明～黄色 |
| Merck | 14,1609 |
| BRN | 1697256 |
| 安定性 | 安定。酸塩化物、酸、酸無水物、強力な酸化剤、二酸化炭素とは混和しません。 |
| InChI | 1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 |
| InChIKey | VHRGRCVQAFMJIZ-UHFFFAOYSA-N |
| SMILES | NCCCCCN |
| LogP（分配係数） | -0.3--0.15 at 21℃ |
| CAS データベース | 462-94-2(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,5-Diaminopentane(462-94-2) |
| EPAの化学物質情報 | Cadaverine (462-94-2) |
化学的特性
colourless to light yellow liquid with a very unpleasant smell
安全性と法規制
| GHS 分類 | DangerH302+H312 (64.2%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oralacute toxicity, dermal]H302 (68.5%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (71%): Harmful in contact with skin [Warning Acute toxicity, dermal]H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H318 (70.4%): Causes serious eye damage [Danger Serious eye damage/eye irritation]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.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Chemical: 1,5-Pentanediamine1,5-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.Status: Active Update: 02-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/16098Status: Active Update: 18-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/277541,5-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. |
| その他の安全情報 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 火災の可能性 | Combustible liquid |
| 有害性の概要 | A strong base that attracts carbon dioxideA skin irritant and possible sensitizer[Merck Index] Causes burns[HSDB] Causes burnsInhalation 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. |
| NFPA Hazard Classification | 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 Products | Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx) |
| Hazard Classes and Categories | Acute Tox. 4 (68.5%)Acute Tox. 4 (71%)Skin Corr. 1B (100%)Eye Dam. 1 (70.4%) |
| Skin, Eye, and Respiratory Irritations | An irritant ... |
| Hazardous Reactivities and Incompatibilities | Materials to avoid Acid chlorides, Acid anhydrides, acids, Strong oxidizing agents, Carbon dioxide (CO2) |
| 消火手順 | Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self contained breathing apparatus for fire fighting if necessary. |
| 保管条件 | Keep 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. |
| 清掃方法 | Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal. Do not let product enter drains. |
| 処分方法 | 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 | 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) | 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 |
| 相互作用 | 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 existaminoguanidine 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. |
| 生態毒性値 | LD50Species: Peromyscus maniculatus (Deer Mouse) oral 1600 mg/kg |
| 環境中動態 | 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). |
| 食品調査値 | 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). |
| 有害作用 | Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| 毒性の概要 | IDENTIFICATION AND USE: Cadaverine is a syrupy, colorless liquid with a distinctive odor of urine and semen. It is soluble in water, ethanolslightly 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 Concentrations | Cadaverine was detected, not quantified in unspecified freshwater and marine algae(1). |
| Effluent Concentrations | Cadaverine was tested for but not detected in gasoline nor diesel exhaust(1). |
| Soil Adsorption/Mobility | 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 | 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 | /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 Sources | Cadaverine'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). |
| F | 10 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | SA0200000 |
| 輸送番号（UN） | UN 2735 8/PG 3 |
| 毒性 | dni-mus:ast 10 mmol/L AMOKAG 33,149,79 |
| 税関コード | 29212900 |
| 危険文句（R） | 34-36/37 |
| 化審法 | (2)-4146 |
| 消防法 | 危-4-2-III |
| 危険表示 | C |
| 安全措置（S） | 26-36/37/39-45-25-27 |
| 危険等級 | 8Eye Dam. 1Skin Corr. 1B |
| 包装等級 | III |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
| 有害物質データ | 462-94-2(Hazardous Substances Data) |
用途
解説
カダベリン，タンパク質の腐敗生成物であるプトマインの一つ．リシンの乾留や発酵，ペンタンジニトリルの還元などで得られる．沸点178～179 ℃．pKa1 10.25，pKa2 9.15．d2540.873．n20D1.463．水，エタノールに可溶．塩酸塩を乾留すると容易にピペリジンになる．皮膚刺激性がある．生理作用は同じポリアミンの一つであるプトレッシンと類似していると考えられている．
使用
1,5-Diaminopentane is mainly used in organic synthesis.
一般的な説明
Cadaverine, 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.
使用用途
1. 生体内物質 カダベリンは、生体内で様々な働きをします。生理作用は他のポリアミンに類似していると考えられており、カダベリンは細胞分裂に必須な増殖因子です。また、RNAを含む核酸やタンパク質の合成を促進する作用があるとされ、新陳代謝を活発にする効果や老化を防ぐ効果、動脈硬化を予防する効果があります。 また、腐敗によって生じるカダベリンやを含む不揮発性アミン類は、ヒスタミン食中毒の原因物質です。体内でヒスタミンの解毒酵素の働きを阻害したり、ヒスタミンの腸管吸収を促進したりする作用があるため、ヒスタミンの作用を増強させます。 リジン代謝異常のある患者の尿からは、カダベリン濃度が上昇していることが確認されています。さらに、カダベリンは細菌性膣炎における悪臭の原因物質の1つです。 2. 高分子材料原料 工業用途として、などのポリアミド合成におけるモノマーに使用されます。
製法・合成法
調製方法
1,5-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.
純化方法
Purify the base by distillation, after standing over KOH pellets (at room temperature, i.e. liquid form). Its dihydrochloride has m 275o (sublimes in a vacuum), and its tetraphenyl boronate has m 164o. [Schwarzenbach et al. Helv Chim Acta 35 2333 1952, Beilstein 4 IV 1310.]