116-31-4

• 常用中文名：视黄醛
• 常用英文名：All-trans-retinal
• CAS号：116-31-4
• 分子式：C₂₀H₂₈O
• 分子量：284.436
• 相关类别： 原料药 维生素类与矿物质类药 维生素AD类药
• 发布时间：2018-06-20 08:17:06
• 更新时间：2024-01-02 09:27:58
• All-trans-retinal是视网膜中主要的维生素A代谢物之一。 在生理条件下,All-trans-retinal 再生为视觉发色团,11-顺式-视黄醛。
• 视黄醛是眼球发育中重要的信号转导分子，其在脊椎动物的眼球发育中具有多种不同的重要作用。近视是一种发育性疾病，近视眼球巩膜的主动扩张是其伸长的重要机制，而视黄醛可能是调节实验性近视眼球伸长的信使分子，有关视黄醛与实验性近视发生，发展的关系的研究取得一定进展，本研究综述了视黄醛及其核受体，实验性近视眼球的视网膜，脉络膜，巩膜的视黄醛改变以及视黄醛作为传递从视网膜到巩膜的眼球伸长信号的信使分子的研究进展情况。 维A酸在皮肤病中的作用非常广泛，但由于局部刺激，一定程度上限制了其临床应用。视黄醛是天然维A酸的中间代谢产物，具有与维A酸相似的生物学活性，而且皮肤对它的耐受性明显优于维A酸。现综述视黄醛在体内及皮肤中的代谢及其生物学活性和在皮肤科中的应用。
  虽然戒烟能够大大降低患肺癌的危险，但就戒烟20年而言，他们患这种癌症的危险仍然要比从不吸烟者大两倍。美国专家的研究结果显示，对于这类戒烟者来说，每天服用适量的视黄醛(即维生素A视黄醇和视黄酸的衍生物)即可进一步有效减少患肺癌的可能。有关研究报告日前发表在《美国癌症研究院院刊》上。得克萨斯大学M.D. Anderson癌症研究中心的Jonathan M. Kurie医学博士等在该项研究中比较了两种不同的视黄醛对226例已戒烟者肺组织中视黄酸beta受体(RAR beta)的影响，这种受体的减少通常被认为是发生前癌性肿瘤的先兆，实验开始时大约有60%的自愿者RAR beta受体数减少。经过服用视黄醛9-cisRA三个月后(每天两次)，发现该组自愿者的RAR beta受体数得到了显著的增加，但服用另一种视黄醛的人却与无效对照组的没有明显差异。此外专家们还认为，视黄醛的这类效应对于那些正在吸烟的人可能会有所不同。

名称

• 中文名: 视黄醛
• 英文名: all-trans-retinal
• 中文别名: 全反式视网膜醛; 维生素 A 醛
• 英文别名: Retinal, all-trans-; Retinene1; all--retinal; 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-Nonatetraenal; retinaldehyde; UNII:RR725D715M; all-trans-retinal; -retinal; all trans-Retinal; all-trans-retinaldehyde; trans-Vitamin A aldehyde; Retinene; EINECS 204-135-8; all-trans Retinal; MFCD00001550; Retinal; trans-Retinal

物化性质

• 密度: 0.9±0.1 g/cm3
• 沸点: 421.4±14.0 °C at 760 mmHg
• 熔点: 61-63°C
• 分子式: C₂₀H₂₈O
• 分子量: 284.436
• 闪点: 205.4±12.4 °C
• 精确质量: 284.214020
• PSA: 17.07000
• LogP: 6.54
• 外观性状: 黄色粉末
• 蒸汽压: 0.0±1.0 mmHg at 25°C
• 折射率: 1.541
• 储存条件: −20°C
• 分子结构:

  五、分子性质数据：

  1、 摩尔折射率：94.14

  2、 摩尔体积（m³/mol）：299.8

  3、 等张比容（90.2K）：729.9

  4、 表面张力（dyne/cm）：35.1

  5、 极化率（10^-24cm³）：37.32

• 计算化学:

  1、 疏水参数计算参考值（XlogP）：6.2

  2、 氢键供体数量：0

  3、 氢键受体数量：1

  4、 可旋转化学键数量：5

  5、 互变异构体数量：

  6、 拓扑分子极性表面积（TPSA）：171

  7、 重原子数量：21

  8、 表面电荷：0

  9、 复杂度：522

  10、 同位素原子数量：0

  11、 确定原子立构中心数量：0

  12、 不确定原子立构中心数量：0

  13、 确定化学键立构中心数量：4

  14、 不确定化学键立构中心数量：0

  15、 共价键单元数量：1

• 更多:

  1. 性状：未确定

  2. 密度（g/mL,25℃）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：64-65

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC, KPa）：未确定

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（mmHg, ºC）：未确定

  12. 饱和蒸气压（kPa, ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：未确定

生物活性

• 描述: All-trans-retinal是视网膜中主要的维生素A代谢物之一。 在生理条件下,All-trans-retinal 再生为视觉发色团,11-顺式-视黄醛。
• 相关类别:
  天然产物 >> 酸和醛
  研究领域 >> 其他
• 靶点:

  Human Endogenous Metabolite

• 参考文献:

  [1]. Sawada O, et al. All-trans-retinal induces Bax activation via DNA damage to mediate retinal cell apoptosis. Exp Eye Res. 2014 Jun;123:27-36.

MSDS

SECTION 1: Identification of the substance/mixture and of the company/undertaking Product identifiers Product name: all trans-Retinal REACH No.: A registration number is not available for this substance as the substance or its uses are exempted from registration, the annual tonnage does not require a registration or the registration is envisaged for a later registration deadline. CAS-No.: 116-31-4 Relevant identified uses of the substance or mixture and uses advised against Identified uses: Laboratory chemicals, Manufacture of substances SECTION 2: Hazards identification Classification of the substance or mixture Classification according to Regulation (EC) No 1272/2008 Acute toxicity, Oral (Category 4), H302 Skin irritation (Category 2), H315 For the full text of the H-Statements mentioned in this Section, see Section 16. Classification according to EU Directives 67/548/EEC or 1999/45/EC Xn HarmfulR22, R38 For the full text of the R-phrases mentioned in this Section, see Section 16. Label elements Labelling according Regulation (EC) No 1272/2008 Pictogram Signal wordWarning Hazard statement(s) H302Harmful if swallowed. H315Causes skin irritation. Precautionary statement(s) none Supplemental Hazardnone Statements Safety data sheet available on request. Other hazards - none SECTION 3: Composition/information on ingredients Substances Synonyms: Vitamin A aldehyde Formula: C20H28O Molecular Weight: 284,44 g/mol CAS-No.: 116-31-4 EC-No.: 204-135-8 Hazardous ingredients according to Regulation (EC) No 1272/2008 ComponentClassificationConcentration Retinaldehyde CAS-No.116-31-4Acute Tox. 4; Skin Irrit. 2;<= 100 % EC-No.204-135-8H302, H315 Hazardous ingredients according to Directive 1999/45/EC ComponentClassificationConcentration Retinaldehyde CAS-No.116-31-4Xn, R22 - R38<= 100 % EC-No.204-135-8 For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16 SECTION 4: First aid measures Description of first aid measures General advice Consult a physician. Show this safety data sheet to the doctor in attendance. If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Flush eyes with water as a precaution. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Most important symptoms and effects, both acute and delayed The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in section 11 Indication of any immediate medical attention and special treatment needed no data available SECTION 5: Firefighting measures Extinguishing media Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special hazards arising from the substance or mixture Carbon oxides Advice for firefighters Wear self contained breathing apparatus for fire fighting if necessary. Further information no data available SECTION 6: Accidental release measures Personal precautions, protective equipment and emergency procedures Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Avoid breathing dust. For personal protection see section 8. Environmental precautions Do not let product enter drains. Methods and materials for containment and cleaning up Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. Reference to other sections For disposal see section 13. SECTION 7: Handling and storage Precautions for safe handling Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Conditions for safe storage, including any incompatibilities Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: -20 °C Light sensitive. Specific end use(s) Apart from the uses mentioned in section 1.2 no other specific uses are stipulated SECTION 8: Exposure controls/personal protection Control parameters Components with workplace control parameters Exposure controls Appropriate engineering controls Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Personal protective equipment Eye/face protection Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Full contact Material: Nitrile rubber Minimum layer thickness: 0,11 mm Break through time: 480 min Material tested:Dermatril® (KCL 740 / Z677272, Size M) Splash contact Material: Nitrile rubber Minimum layer thickness: 0,11 mm Break through time: 480 min Material tested:Dermatril® (KCL 740 / Z677272, Size M) data source: KCL GmbH, D-36124 Eichenzell, phone +49 (0)6659 87300, test method: EN374 If used in solution, or mixed with other substances, and under conditions which differ from EN 374, contact the supplier of the CE approved gloves. This recommendation is advisory only and must be evaluated by an industrial hygienist and safety officer familiar with the specific situation of anticipated use by our customers. It should not be construed as offering an approval for any specific use scenario. Body Protection Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Respiratory protection For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Control of environmental exposure Do not let product enter drains. SECTION 9: Physical and chemical properties Information on basic physical and chemical properties a) AppearanceForm: powder b) Odourno data available c) Odour Thresholdno data available d) pHno data available e) Melting point/freezingMelting point/range: 62 - 64 °C point f) Initial boiling point and no data available boiling range g) Flash pointno data available h) Evapouration rateno data available i) Flammability (solid, gas) no data available j) Upper/lowerno data available flammability or explosive limits k) Vapour pressureno data available l) Vapour densityno data available m) Relative densityno data available n) Water solubilityno data available o) Partition coefficient: n- no data available octanol/water p) Auto-ignitionno data available temperature q) Decompositionno data available temperature r) Viscosityno data available s) Explosive propertiesno data available t) Oxidizing propertiesno data available Other safety information no data available SECTION 10: Stability and reactivity Reactivity no data available Chemical stability Stable under recommended storage conditions. Possibility of hazardous reactions no data available Conditions to avoid no data available Incompatible materials Oxidizing agents Hazardous decomposition products Other decomposition products - no data available In the event of fire: see section 5 SECTION 11: Toxicological information Information on toxicological effects Acute toxicity no data available Skin corrosion/irritation no data available Serious eye damage/eye irritation no data available Respiratory or skin sensitisation no data available Germ cell mutagenicity mouse lymphocyte DNA inhibition rat mammary gland DNA inhibition Carcinogenicity IARC:No component of this product present at levels greater than or equal to 0.1% is identified as probable, possible or confirmed human carcinogen by IARC. Reproductive toxicity Laboratory experiments have shown teratogenic effects. Specific target organ toxicity - single exposure no data available Specific target organ toxicity - repeated exposure no data available Aspiration hazard no data available Additional Information RTECS: VH6407000 Gastrointestinal disturbance, Repeated exposure may cause skin dryness or cracking., Headache SECTION 12: Ecological information Toxicity no data available Persistence and degradability no data available Bioaccumulative potential no data available Mobility in soil no data available Results of PBT and vPvB assessment PBT/vPvB assessment not available as chemical safety assessment not required/not conducted Other adverse effects no data available SECTION 13: Disposal considerations Waste treatment methods Product Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging Dispose of as unused product. SECTION 14: Transport information UN number ADR/RID: -IMDG: -IATA: - UN proper shipping name ADR/RID: Not dangerous goods IMDG: Not dangerous goods IATA:Not dangerous goods Transport hazard class(es) ADR/RID: -IMDG: -IATA: - Packaging group ADR/RID: -IMDG: -IATA: - Environmental hazards ADR/RID: noIMDG Marine pollutant: noIATA: no Special precautions for user no data available SECTION 15 - REGULATORY INFORMATION N/A SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 1、 致突变：大鼠乳腺DNA抑制：3umol/L 小鼠淋巴细胞DNA抑制：100umol/L CHEMICAL IDENTIFICATION RTECS NUMBER : VH6407000 CHEMICAL NAME : Retinal, all-trans- CAS REGISTRY NUMBER : 116-31-4 BEILSTEIN REFERENCE NO. : 1914183 LAST UPDATED : 199701 DATA ITEMS CITED : 3 MOLECULAR FORMULA : C20-H28-O MOLECULAR WEIGHT : 284.48 HEALTH HAZARD DATA ACUTE TOXICITY DATA MUTATION DATA TYPE OF TEST : DNA inhibition TEST SYSTEM : Rodent - mouse Lymphocyte DOSE/DURATION : 100 umol/L REFERENCE : ONCOBS Oncology. (S. Karger AG, Postfach CH-4009 Basel, Switzerland) V.21- 1967- Volume(issue)/page/year: 44,356,1987

安全

• 符号: GHS07
• 信号词: Warning
• 危害声明: H302-H315
• 个人防护装备: dust mask type N95 (US);Eyeshields;Gloves
• 危害码 (欧洲): Xn: Harmful;
• 风险声明 (欧洲): 22-38
• 安全声明 (欧洲): S22-S36/37
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 3
• RTECS号: VH6407000
• 海关编码: 2912299000

合成路线

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制备

维生素A在经醇脱氢酶及辅酶Ｉ、ＩＩ的催化，形成顺、反两种视黄醛。

海关

海关编码	2912299000
中文概述	2912299000. 其他不含其他含氧基的环醛. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:5.5%. 普通关税:30.0%
申报要素	品名, 成分含量, 用途, 四聚甲醛报明外观
Summary	2912299000. other cyclic aldehydes without other oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%