(6Z,9Z,12Z,15Z)-十八碳四烯酸甲酯 | 73097-00-4

• 物质功能分类: 分析化学 - 标准品 - 分析标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (6Z,9Z,12Z,15Z)-十八碳四烯酸甲酯
• 中文别名: 硬脂酸甲酯
• 英文名称: (6Z,9Z,12Z,15Z)-octadecatetraenoic acid methyl ester
• 英文别名: 6,9,12,15-cis-octadecanetetraenoic acid methyl ester；methyl 6Z,9Z,12Z,15Z-octadecatetraenoate；methyl 6,9,12,15-octadecatetraenoate；stearidonic acid methyl ester；methyl stearidonate；methyl (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoate
• CAS: 73097-00-4
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: BIRKCHKCDPCDEG-GJDCDIHCSA-N

物化性质

• 沸点：
  374.5±31.0 °C(Predicted)
• 密度：
  0.907±0.06 g/cm3(Predicted)
• 闪点：
  13 °C
• 溶解度：
  DMF：50mg/mL； DMSO：50mg/mL；乙醇：50mg/mL； PBS（pH 7.2）：0.15 mg/mL
• 保留指数：
  2088.4

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  F
• 安全说明：
  S16
• 危险类别码：
  R11
• 危险品运输编号：
  UN 1170 3/PG 2
• 储存条件：
  | -20°C |

SDS

Date Updated: 10/FEB/2006
Version 1.1
Regulation (EC) No 1907/2006
________________________________________________________________________
1 - Product and Company Information
________________________________________________________________________
Product Name CIS-6,9,12,15-OCTADECATETRAENOIC ACID
METHYL ESTER
Product Number O5130
Company
Century Ba-Shi Building 22A-B,
200020 Shanghai
Technical Phone # [phone]
Fax [phone]
E-mail Address
________________________________________________________________________
2 - Hazards Identification
________________________________________________________________________
SPECIAL INDICATION OF HAZARDS TO HUMANS AND THE ENVIRONMENT
Not hazardous according to Directive 67/548/EEC.
________________________________________________________________________
3 - Composition/Information on Ingredients
________________________________________________________________________
Product Name CAS # EC no Annex I
Index Number
METHYL STEARIDONATE 73097-00-4 None None
Formula C19H30O2
Molecular Weight 290,4400 AMU
Synonyms Stearidonic acid methyl ester *
cis-6,9,12,15-Octadecatetraenoic acid methyl
ester
________________________________________________________________________
4 - First Aid Measures
________________________________________________________________________
AFTER INHALATION
If inhaled, remove to fresh air. If breathing becomes difficult,
call a physician.
AFTER SKIN CONTACT
In case of contact, immediately wash skin with soap and copious
amounts of water.
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.
________________________________________________________________________
5 - Fire Fighting Measures
________________________________________________________________________
EXTINGUISHING MEDIA
Suitable: Water spray. Carbon dioxide, dry chemical powder, or
appropriate foam.
SPECIAL RISKS
Specific Hazard(s): Emits toxic fumes under fire conditions.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.
________________________________________________________________________
6 - Accidental Release Measures
________________________________________________________________________
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.
________________________________________________________________________
7 - Handling and Storage
________________________________________________________________________
HANDLING
Directions for Safe Handling: Avoid inhalation. Avoid contact
with eyes, skin, and clothing. Avoid prolonged or repeated
exposure.
STORAGE
Conditions of Storage: Keep tightly closed.
Store at -20°C
________________________________________________________________________
8 - Exposure Controls / Personal Protection
________________________________________________________________________
ENGINEERING CONTROLS
Safety shower and eye bath. Mechanical exhaust required.
GENERAL HYGIENE MEASURES
Wash thoroughly after handling.
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: Protective gloves.
Eye Protection: Chemical safety goggles.
________________________________________________________________________
9 - Physical and Chemical Properties
________________________________________________________________________
Appearance Physical State: Liquid
Color: Colorless
Form: Clear 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
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A
________________________________________________________________________
10 - Stability and Reactivity
________________________________________________________________________
STABILITY
Stable: Stable.
Materials to Avoid: Strong oxidizing agents.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide.
HAZARDOUS POLYMERIZATION
Hazardous Polymerization: Will not occur
________________________________________________________________________
11 - Toxicological Information
________________________________________________________________________
SIGNS AND SYMPTOMS OF EXPOSURE
To the best of our knowledge, the chemical, physical, and
toxicological properties have not been thoroughly investigated.
ROUTE OF EXPOSURE
Skin Contact: May cause skin irritation.
Skin Absorption: May be harmful if absorbed through the skin.
Eye Contact: May cause eye irritation.
Inhalation: Material may be irritating to mucous membranes and
upper respiratory tract. May be harmful if inhaled.
Ingestion: May be harmful if swallowed.
________________________________________________________________________
12 - Ecological Information
________________________________________________________________________
No data available.
________________________________________________________________________
13 - Disposal Considerations
________________________________________________________________________
SUBSTANCE DISPOSAL
Contact a licensed professional waste disposal service to dispose
of this material. 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.
________________________________________________________________________
14 - Transport Information
________________________________________________________________________
RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
IATA
Non-hazardous for air transport.
________________________________________________________________________
15 - Regulatory Information
________________________________________________________________________
Not hazardous according to Directive 67/548/EEC.
Caution: Substance not yet fully tested (EU).
COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification
________________________________________________________________________
16 - Other Information
________________________________________________________________________
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
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.
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.

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模块 15 - 法规信息
N/A

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模块16 - 其他信息
N/A

反应信息

• 作为反应物：
  描述：

  (6Z,9Z,12Z,15Z)-十八碳四烯酸甲酯 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以62%的产率得到顺6,9,12,15-十八碳四烯酸
  参考文献：
  名称：

  Synthesis of Rare Polyunsaturated Fatty Acids: Stearidonic and ω-3 Arachidonic

  摘要：

  对具有潜在抗炎活性的稀有天然 ω-3 C18 和 C20 脂肪酸进行了全化学合成，以便对其生物活性进行后续研究。

  DOI：

  10.1007/s10600-015-1485-3
• 作为产物：
  描述：

  全顺式二十碳五烯酸 在 六甲基磷酰三胺 、 copper(l) iodide 、 正丁基锂 、 碘 、 二异丁基氢化铝 、 potassium hydrogencarbonate 、 高碘酸 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 9.5h， 生成 (6Z,9Z,12Z,15Z)-十八碳四烯酸甲酯
  参考文献：
  名称：

  Concise syntheses of three ω-3 polyunsaturated fatty acids

  摘要：

  The synthesis of the three omega-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.009

文献信息

• Sarcoglycosides A - C, New<i>O</i>-Glycosylglycerol Derivatives from the South China Sea Soft Coral<i>Sarcophyton infundibuliforme</i>
  作者：Liang Li、Chang-Yun Wang、Chang-Lun Shao、Yue-Wei Guo、Guo-Qiang Li、Xue-Ping Sun、Lei Han、Hui Huang、Hua-Shi Guan

  DOI：10.1002/hlca.200900026

  日期：2009.8

  Chemical examination of the soft coral Sarcophyton infundibuliforme collected from the South China Sea resulted in the isolation of the three new O‐glycosylglycerol derivatives sarcoglycosides A–C (1–3), together with two known compounds, chimyl alcohol (4) and hexadecanol (5). Their structures were elucidated by combined spectral and chemical methods. All the compounds showed moderate toxicity to

  软的化验珊瑚Sarcophyton infundibuliforme从中国南海收集导致三个新的隔离ø -glycosylglycerol衍生物sarcoglycosides A-C（1 - 3）具有两个公知的化合物，鲛肝醇（一起4）和十六醇（5）。通过结合光谱和化学方法阐明了它们的结构。所有化合物对盐水虾卤虫盐沼均显示中度毒性。
• [EN] ASCORBATE ESTERS OF OMEGA-3 FATTY ACIDS<br/>[FR] ESTERS D'ASCORBATE D'ACIDES GRAS OMÉGA 3
  申请人：JIVA PHARMA INC

  公开号：WO2014134053A1

  公开（公告）日：2014-09-04

  The present invention provides ascorbate esters of omega-3 fatty acids as their pharmaceutically-acceptable salts and pharmaceutically- acceptable formulations for use as dietary supplements with enhanced antioxidant properties, in improving the effectiveness of other drugs and in treatment of hypertriglyceridemia, hypercholestolemia, diabetes, psychiatric and neurological disorders, attention deficit and hyperactivity disorder, and as cosmeceuticals.

  本发明提供了抗坏血酸酯化的ω-3脂肪酸及其药学上可接受的盐和制剂，用作具有增强抗氧化性能的膳食补充剂，在提高其他药物的有效性以及治疗高三酰甘油血症、高胆固醇血症、糖尿病、精神和神经障碍、注意力缺陷和多动症以及作为化妆品成分。
• An allelopathic fatty acid from the brown alga Cladosiphon okamuranus
  作者：Hiroshi Kakisawa、Fumika Asari、Takenori Kusumi、Takeshi Toma、Takemaro Sakurai、Takeshi Oohusa、Yoshiaki Hara、Mitsuo Chiharai

  DOI：10.1016/0031-9422(88)84084-6

  日期：1988.1

  Abstract An allelopathic substance was isolated from the methanol extract of the brown alga, Cladosiphon okamuranus . Extraction and purification of the active substance was monitored by bioassays against the conchospores of Porphyra yezoensis and Heterosigma akashiwo . The compound was identified as 6 Z ,9 Z ,12 Z ,15 Z -octadecatetraenoic acid and its activity was then tested against 36 species of

  摘要 从褐藻Cladosiphon okamuranus 的甲醇提取物中分离出一种化感物质。活性物质的提取和纯化通过针对条斑紫菜和赤石异星孢子的生物测定进行监测。该化合物被鉴定为 6 Z ,9 Z ,12 Z ,15 Z-十八碳四烯酸，然后测试其对 36 种微藻的活性。许多测试的真核生物在 5 ppm 时受到影响，但原核生物在 25 ppm 时不受影响。四不饱和脂肪酸以 1 ppm 的浓度消灭了有毒的赤潮浮游生物，例如 Chattonella antiqua。
• Monoepoxy octadecadienoates and monoepoxy octadecatrienoates
  作者：Pei H. Cui、Rujee K. Duke、Colin C. Duke

  DOI：10.1016/j.chemphyslip.2008.02.003

  日期：2008.4

  correlated spectroscopy (COSY) and 1H-13C heteronuclear correlation (HETCOR). The proton and carbon NMR chemical shifts of the epoxide, the double bonds, and the interrupted methylenes are assigned. Also discussed is an interpretation of the 1H and 13C NMR spectra of these monoepoxides including the changes in the 13C resonance of the olefinic carbons on the neighboring double bonds resulting from epoxide

  使用间氯过苯甲酸将γ-亚麻酸，α-亚麻酸和十八碳四烯酸的甲酯环氧化，得到九种顺式-单环氧-C18脂肪酸甲酯（FAME），包括新型的十八烷基-甲基-顺式-单环氧衍生物和γ-亚麻酸的顺式-6,7-环氧衍生物。这九种单环氧FAME通过正相HPLC纯化，通过LC-MS，1H和13C NMR鉴定，并通过质谱和NMR光谱进行表征。这项研究的重点是使用NMR光谱技术，包括1H，13C，1H-1H相关光谱（COSY）和1H-13C异核相关（HETCOR），对这些C18单环氧FAME进行结构表征。确定了环氧化物，双键和间断亚甲基的质子和碳NMR化学位移。
• Chemical C2-elongation of polyunsaturated fatty acids
  作者：Dmitry V. Kuklev、William L. Smith

  DOI：10.1016/j.chemphyslip.2006.09.002

  日期：2006.11

  Three fatty acids were synthesized from commercially available alpha-linolenic, stearidonic and eicosapentaenoic acids by C2-elongation using a four step preparative technique. The parent fatty acid methyl esters were reduced to alcohols with LiAlH4, converted to bromides by treatment with triphenylphosphine dibromide, coupled with a lithiated C2-elongation block -2,4,4-trimethyl-2-oxazoline - to form the corresponding 2,2-dimethyloxazolines of C2-elongated fatty acids, and finally, converted to the target polyunsaturated fatty acids by acidic alcoholysis. Yields of more than 60% were achieved on a gram scale. The resulting 11Z, 14Z, 17Z-eicosatrienoic, 8Z, 11Z, 14Z, 17Z-eicosatetraenoic and 7Z, 10Z,13Z, 16Z, 19Z-docosapentaenoic acids were obtained as colorless oils with > 98% purity and could be used for biochemical investigations without additional purification. The elongated fatty acids were free of byproducts that could result from Z-E isomerization or migration of double bonds. (c) 2006 Elsevier Ireland Ltd. All rights reserved.