arachidonyl alcohol | 13487-46-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: arachidonyl alcohol
• 英文别名: (5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraen-1-ol；(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-ol
• CAS: 13487-46-2
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: NYBCZSBDKXGAGM-DOFZRALJSA-N

物化性质

• 沸点：
  402.6±24.0 °C(Predicted)
• 密度：
  0.878±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：250 mg/mL（860.64 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 海关编码：
  2905290000

SDS

Version 1.2
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name ARACHIDONYL ALCOHOL APPROX 99%

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2 - Hazards Identification

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
ARACHIDONYL ALCOHOL APPROX 99% 13487-46-2 None None
Formula C20H34O
Molecular Weight 290,5000 AMU

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If breathing becomes difficult,
call a physician.
AFTER SKIN CONTACT
In case of skin contact, flush with copious amounts of water for
at least 15 minutes. Remove contaminated clothing and shoes.
Call a physician.
AFTER EYE CONTACT
In case of contact with eyes, flush with copious amounts of
water for at least 15 minutes. Assure adequate flushing by
separating the eyelids with fingers. Call a physician.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician.

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5 - Fire Fighting Measures

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EXTINGUISHING MEDIA
Suitable: Carbon dioxide, dry chemical powder, or appropriate
SIGMA www.molbase.com
foam.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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PROCEDURE(S) OF PERSONAL PRECAUTION(S)
Wear protective equipment.
METHODS FOR CLEANING UP
Absorb on sand or vermiculite and place in closed containers for
disposal. Ventilate area and wash spill site after material
pickup is complete.

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7 - Handling and Storage

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STORAGE
Store at -20°C

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Mechanical exhaust required.
PERSONAL PROTECTIVE EQUIPMENT
Respiratory Protection: Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US)
or CEN (EU). Respiratory protection is not required. Where
protection is desired, use multi-purpose combination (US) or type
ABEK (EN 14387) respirator cartridges.
Hand Protection: Compatible chemical-resistant gloves.
Eye Protection: Chemical safety goggles.

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9 - Physical and Chemical Properties

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Appearance Physical State: Liquid
Property Value At Temperature or Pressure
pH N/A
BP/BP Range N/A
MP/MP Range N/A
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
SIGMA www.molbase.com
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Stable: Stable.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide.
HAZARDOUS POLYMERIZATION
Hazardous Polymerization: Will not occur

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11 - Toxicological Information

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ROUTE OF EXPOSURE
Multiple Routes: May cause irritation. May be harmful by
inhalation, ingestion, or skin absorption.
CONDITIONS AGGRAVATED BY EXPOSURE
The toxicological properties have not been thoroughly
investigated.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SUBSTANCE DISPOSAL
Dissolve or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner and
scrubber. Observe all federal, state, and local environmental
regulations.

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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Caution: Substance not yet fully tested (EU).
COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification

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16 - Other Information
SIGMA www.molbase.com

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
SIGMA www.molbase.com

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Arachidonyl alcohol 是一种长链伯脂肪醇。它可以用作生产醚脂质的底物。

靶点

• IC50: 作为醚脂质的底物

体外研究

• Arachidonyl alcohol 可以从 arachidonic acid 转化而来，然后在细胞内累积成为蜡酯。
• 新菌株 Acinetobacter 物种 N-476-2 能够有效将 arachidonic acid 转化为 arachidonyl alcohol。

反应信息

• 作为反应物：
  描述：

  arachidonyl alcohol 在 盐酸 、 sodium hydroxide 、 sodium 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 乙醇 、 二乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 7.0h， 生成 廿二碳四烯酸
  参考文献：
  名称：

  Kuklev; Popkov; Kas'yanov, Russian Journal of Bioorganic Chemistry, 1996, vol. 22, # 3, p. 192 - 195

  摘要：

  DOI：
• 作为产物：
  描述：

  花生四烯酸 在 吡啶 、 甲醇 、 sodium tetrahydroborate 、 三聚氟氰 作用下， 生成 arachidonyl alcohol
  参考文献：
  名称：

  羧酸一键选择性转化为醇。

  摘要：

  通过用硼氢化钠化学选择性还原其相应的氟化物并滴加甲醇，可将羧酸转化为醇。该方法通用且温和，并且显示出高水平的官能团相容性。由N-保护的氨基和肽醇，带有各种保护基，可以由它们相应的氨基酸和肽以相同的方式制备，而无需消旋。

  DOI：

  10.1021/jo9520699

文献信息

• N-(HETERO)ARYL-PYRROLIDINE DERIVATIVES OF PYRAZOL-4-YL-PYRROLO[2,3-d]PYRIMIDINES AND PYRROL-3-YL-PYRROLO[2,3-d]PYRIMIDINES AS JANUS KINASE INHIBITORS
  申请人：Rodgers James D.

  公开号：US20100298334A1

  公开（公告）日：2010-11-25

  The present invention relates to N-(hetero)aryl-pyrrolidine derivatives of Formula I: which are JAK inhibitors, such as selective JAK1 inhibitors, useful in the treatment of JAK-associated diseases including, for example, inflammatory and autoimmune disorders, as well as cancer.

  本发明涉及式I的N-(杂)芳基吡咯烷衍生物： 这些是JAK抑制剂，如选择性JAK1抑制剂，在治疗JAK相关疾病方面具有用处，例如炎症和自身免疫性疾病，以及癌症。
• Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches
  作者：Patrick Pfaff、Felix Anderl、Moritz Fink、Moritz Balkenhohl、Erick M. Carreira

  DOI：10.1021/jacs.1c06014

  日期：2021.9.15

  TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates. In situ desilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine

  我们报告了一种针对新型芳基氮并三唑光开关及其光物理特性的模块化方法。锂化 TIPS-乙炔与芳基重氮四氟硼酸盐的加成得到范围广泛的偶氮乙炔，构成了一类尚未开发的稳定中间体。原位脱硅瞬时导致末端芳基偶氮乙炔发生铜催化环加成反应 (CuAAC)，并产生多种有机叠氮化物。这些包括源自天然产物或药物的复杂分子，例如秋水仙碱、紫杉醇、达菲和花生四烯酸。芳基氮并三唑显示近定量光异构化和长热Z-半条命。使用该方法，我们首次介绍了联乙炔平台的设计和合成。它允许实施连续和面向多样性的方法，将两种不同的偶联物连接到一个常见的光开关偶氮三唑中的独立可寻址乙炔。这在几种光开关偶联物的合成中得到了展示，具有作为 photoPROTAC 和生物素偶联物的潜在应用。
• Cannabimimetic lipid amides as useful medications
  申请人：University of Connecticut

  公开号：US07161016B1

  公开（公告）日：2007-01-09

  Novel analogs of arachidonylethanolamide are presented which have higher affinities for the cannabinoid CB1 and/or CB2 receptor sites. Further, most of the analogs exhibit greater metabolic stability than arachidonylethanolamide. The improved receptor affinity and selectivity and/or greater metabolic stability make these analogs therapeutically useful as medications for relief of pain caused by cancer and nausea caused by chemotherapy, as well as for peripheral pain. The compounds may also be useful as oral and topical contraceptives, in suppression of the immune system, enhancement of appetite and in treatment of psychomotor disorders, multiple sclerosis and hypertension.

  新型的花生四烯酰乙醇胺类似物具有更高的亲和力，适用于大麻素CB1和/或CB2受体位点。此外，大多数类似物表现出比花生四烯酰乙醇胺更高的代谢稳定性。改善的受体亲和力和选择性和/或更高的代谢稳定性使这些类似物在作为药物用于缓解癌症引起的疼痛和化疗引起的恶心，以及外周疼痛方面具有治疗用途。这些化合物也可能用于口服和局部避孕药、免疫系统抑制、增强食欲以及治疗精神运动障碍、多发性硬化和高血压。
• [EN] FATTY ACID DERIVATIVES FOR TREATING NON-ALCOHOLIC STEATOHEPATITIS<br/>[FR] DÉRIVÉS D'ACIDE GRAS POUR LE TRAITEMENT DE LA STÉATOHÉPATITE NON ALCOOLIQUE
  申请人：BASF AS

  公开号：WO2019111048A1

  公开（公告）日：2019-06-13

  The present disclosure provides a compound for use in therapeutic and/or prophylactic treatment of non-alcoholic steatohepatitis (NASH) and/or alcoholic steatohepatitis (ASH). The compound for use according to the invention, is an unsaturated fatty acid with an oxygen incorporated in the β-position, and further comprising an α-substituent. More particularly, the invention provides a compound for use in treatment of NASH and/or ASH, and a method using this, wherein the compound is of Formula (II), wherein R1, R2, R3, X, and Y are as defined in the specification; and wherein this compound may be administered alone or in combination with an additional active agent.

  本公开提供了一种用于治疗和/或预防非酒精性脂肪肝炎（NASH）和/或酒精性脂肪肝炎（ASH）的化合物。根据本发明使用的化合物是一种在β位含有氧原子的不饱和脂肪酸，并且还包含一个α-取代基。更具体地说，本发明提供了一种用于治疗NASH和/或ASH的化合物以及使用该方法，其中该化合物是公式（II），其中R1、R2、R3、X和Y如说明书中所定义；并且该化合物可以单独使用或与另一种活性剂结合使用。
• [EN] LIPID COMPOUNDS AND COMPOSITIONS AND THEIR OPTHALMIC USE<br/>[FR] COMPOSÉS LIPIDIQUES ET COMPOSITIONS ASSOCIÉES ET LEUR UTILISATION OPHTALMIQUE
  申请人：BIOZEP AS

  公开号：WO2017093732A1

  公开（公告）日：2017-06-08

  The invention relates to lipid compounds of formula (I) and their pharmaceutically acceptable salts for the prevention and/or treatment of ophthalmic disorders such as retinal degenerative disorders and ocular inflammatory diseases: (I) (wherein R1 is either a C9 to C22 alkyl group, or a C9 to C22 alkenyl group having from 1 to 6 double bonds; R2 is selected from the group consisting of a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an alkylthio group, a carboxy group, an acyl group, an amino group, and an alkylamino group; R3 is a hydrogen atom, or a group R2; R4 is a carboxylic acid or a derivative thereof; and X is methylene (-CH2-), or an oxygen or sulfur atom).

  本发明涉及用于预防或治疗如视网膜退行性疾病和眼部炎症疾病的眼科疾病的一类脂质化合物公式(I)及其药用可接受盐：(I)（其中R1为C9至C22的烷基或具有1至6个双键的C9至C22的烯基；R2选自卤素原子、羟基、烷基、烷氧基、烷硫基、羧基、酰基、氨基和烷基氨基的组；R3为氢原子或R2基团；R4为羧酸或其衍生物；X为亚甲基(-CH2-)，或氧或硫原子）。