cis-15-十四酸甲酯 | 2733-88-2

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 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: cis-15-十四酸甲酯
• 中文别名: 顺式-15-二十四烯酸甲酯；神经酸甲酯；CIS-15-二十四烯酸甲酯
• 英文名称: nervonic acid methyl ester
• 英文别名: methyl nervonate；methyl 15(Z)-tetracosenoate；Methyl (Z)-tetracos-15-enoate
• CAS: 2733-88-2
• 化学式: C₂₅H₄₈O₂
• 分子量: 380.655
• InChiKey: AINIZSBLAFHZCP-KHPPLWFESA-N

物化性质

• 熔点：
  14-15℃ (acetone )
• 沸点：
  186-202℃
• 密度：
  0.868±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：20 mg/ml； DMSO：20 mg/ml；乙醇：100 mg/ml
• LogP：
  11.075 (est)
• 保留指数：
  2680

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  27
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：
  Xi
• 安全说明：
  S26,S36/37
• 危险类别码：
  R36/37/38
• WGK Germany：
  1
• 海关编码：
  2916190090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  | -20°C |

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Methyl cis-15-tetracosenoate
CAS-No. : 2733-88-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Nervonic acid methyl ester
Selacholeic acid methyl ester
Formula : C25H48O2
Molecular Weight : 380,65 g/mol
Component Concentration
Methyl (Z)-tetracos-15-enoate
CAS-No. 2733-88-2 -
EC-No. 220-352-0

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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
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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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

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities
Store in cool place. 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.
Recommended storage temperature: -20 °C
Light sensitive. Store under inert gas.
Specific end uses
no data available

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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.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose 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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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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 sensitization
no data available
Germ cell mutagenicity
no data available
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
no data available
Specific target organ toxicity - single exposure
no data available
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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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
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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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: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

顺式-15-四羧酸甲酯是一种生物化学试剂，可用于生物材料或有机化合物的研究，在生命科学领域有着广泛的应用价值。

反应信息

• 作为反应物：
  描述：

  cis-15-十四酸甲酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 神经酸
  参考文献：
  名称：

  一种简便有效的合成标记和未标记的超长链多不饱和脂肪酸的方法

  摘要：

  有几种方法可用于延长脂肪酸酰基链。本文描述了以前发布的协议对烷基溴的锰基Wurtz型偶联方法对脂肪酸领域的适应性。22-Bromo-3（Z），6（Z），9（Z），12（Z），15（Z），18（Z）-二十二碳六烯，很容易从4（Z），7（Z），10制备（Z），13（Z），16（Z），19（Z二十二碳六烯酸通过在锰粉，镍催化剂和三联吡啶存在下于40°C搅拌4小时与同源ω-溴酸酯偶联。这产生了一系列链长为32–40的碳的ω3-己烯酸酯系列，产率为70–75％。皂化和最终纯化后，获得纯度> 98％的相应脂肪酸。通过使用甲基[2,2,3,3,4,4- 2 ħ 6 ] 10 bromodecanoate作为偶联伙伴有可能在同位素标记的形式制备一个非常长链脂肪酸，即[2,2,3 ，3,4,4- 2 ħ 6 ] 14（ž），17（ž），20（ž），23（ž），26（ž），29（ž）-十二碳六烯酸。还制备了单

  DOI：

  10.1002/aocs.12484
• 作为产物：
  描述：

  油酸甲酯 在 锰 、 lithium aluminium tetrahydride 、 氯化镍二甲氧基乙烷 、 4,4',4''-三叔丁基2,2',6'2''-曲吡啶 、 二溴三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 cis-15-十四酸甲酯
  参考文献：
  名称：

  一种简便有效的合成标记和未标记的超长链多不饱和脂肪酸的方法

  摘要：

  有几种方法可用于延长脂肪酸酰基链。本文描述了以前发布的协议对烷基溴的锰基Wurtz型偶联方法对脂肪酸领域的适应性。22-Bromo-3（Z），6（Z），9（Z），12（Z），15（Z），18（Z）-二十二碳六烯，很容易从4（Z），7（Z），10制备（Z），13（Z），16（Z），19（Z二十二碳六烯酸通过在锰粉，镍催化剂和三联吡啶存在下于40°C搅拌4小时与同源ω-溴酸酯偶联。这产生了一系列链长为32–40的碳的ω3-己烯酸酯系列，产率为70–75％。皂化和最终纯化后，获得纯度> 98％的相应脂肪酸。通过使用甲基[2,2,3,3,4,4- 2 ħ 6 ] 10 bromodecanoate作为偶联伙伴有可能在同位素标记的形式制备一个非常长链脂肪酸，即[2,2,3 ，3,4,4- 2 ħ 6 ] 14（ž），17（ž），20（ž），23（ž），26（ž），29（ž）-十二碳六烯酸。还制备了单

  DOI：

  10.1002/aocs.12484

文献信息

• NickelButadiene Catalytic System for the Cross-Coupling of Bromoalkanoic Acids with Alkyl Grignard Reagents: A Practical and Versatile Method for Preparing Fatty Acids
  作者：Takanori Iwasaki、Kiyokazu Higashikawa、Vutukuri P. Reddy、Willbe W. S. Ho、Yukari Fujimoto、Koichi Fukase、Jun Terao、Hitoshi Kuniyasu、Nobuaki Kambe

  DOI：10.1002/chem.201204222

  日期：2013.2.25

  The knights who say Ni: A practical and convenient synthetic route to fatty acids involves the Ni‐catalyzed alkylalkyl cross‐coupling of bromoalkanoic acids and alkyl Grignard reagents in the presence of 1,3‐butadiene as an additive (see scheme).

  说Ni的骑士们：一种实用且方便的合成脂肪酸途径涉及在1,3-丁二烯作为添加剂的情况下，Ni催化的溴链烷酸与烷基Grignard试剂的烷基烷基交叉偶联（参见方案）。
• Oxygenation of Monoenoic Fatty Acids by CYP175A1, an Orphan Cytochrome P450 from <i>Thermus thermophilus</i> HB27
  作者：Sandeep Goyal、Shibdas Banerjee、Shyamalava Mazumdar

  DOI：10.1021/bi300514j

  日期：2012.10.9

  monooxygenation of the monoenoic fatty acids depending on the ethylenic double bond (C═C) configuration. When the double bond was in cis-configuration, an epoxy fatty acid was found to be the major product and two allyl-hydroxy fatty acids were found to be the minor products. But when the double bond was in trans-configuration the product distribution was reversed. The oxygenation efficiency was found to be

  已经研究了CYP175A1对各种链长（C16–C24）的饱和和单不饱和脂肪酸的单加氧反应的催化活性，以评估该孤儿热稳定细胞色素P450酶的酶促性质。结果表明，该酶可以催化单不饱和脂肪酸的反应，但不能催化饱和脂肪酸的反应。使用ESI-MS和GC-MS进行的产品分析表明，取决于烯键式双键（C═C）的构型，CYP175A1催化单烯脂肪酸的单加氧反应具有重要的区域选择性。当双键处于顺式构型时，发现环氧脂肪酸是主要产物，而发现两个烯丙基-羟基脂肪酸是次要产物。但是当双键处于反式构型时，产物分布相反。发现棕榈油酸的氧化效率最高（链长为C16），但活性与链长或脂肪酸的不饱和位置没有直接关系。分子对接计算表明，单烯脂肪酸的“ U”型构型特别负责它们在酶口袋中的结合，这也与在氧化反应中观察到的区域选择性一致。目前的结果提供证据，CYP175A1可以催化几种单烯脂肪酸的区域选择性氧化反应，尽管它不能催化相应的
• METHODS OF TREATING MEIBOMIAN GLAND DYSFUNCTION
  申请人：Dalton James T.

  公开号：US20110172302A1

  公开（公告）日：2011-07-14

  The present invention includes methods for treating Meibomian gland dysfunctions. The invention also includes methods for improving tear lipid composition, for treating abnormal Meibomian gland secretion and for normalizing Meibomian gland secretions.

  本发明涉及治疗美波腺功能障碍的方法。该发明还包括改善泪液脂质组成的方法，治疗异常的美波腺分泌以及规范美波腺分泌的方法。
• 一种神经酸的制备方法及神经酸
  申请人：西北农林科技大学

  公开号：CN111423320B

  公开（公告）日：2022-11-29

  本发明公开了一种神经酸的制备方法及神经酸，包括：利用1‑溴‑顺‑13‑二十二碳烯制备格式试剂，格氏试剂、碘化亚铜和环氧乙烷经过格氏试剂的环氧开环反应合成1‑羟基‑顺‑15‑二十四碳烯；1‑羟基‑顺‑15‑二十四碳烯、醋酸碘苯和TEMPO经过氧化反应制备得到神经酸。通过化学合成的手段，以芥酸为原料，通过酯化，还原，溴代，格氏反应，氧化，完成了神经酸的合成。本发明合成神经酸的方法具有原料价廉易得，易操作，收率高，产品纯度高等优点。
• Nervonic acid derivatives, their preparation and use
  申请人：Croda International PLC

  公开号：US06664406B1

  公开（公告）日：2003-12-16

  The present invention relates to a nervonic acid derivatives of formula (I) CH3—(CH2)7—CH═CH—(CH2)13—C(O)—O—(CH2)3—OR  (I) wherein R is hydrogen (H) or a residue of a carboxylic acid; or a salt of the compound where R is H; or a bioprecursor, prodrug thereof. Those compounds wherein R is other than H have pharmacological activity, in particular anti-inflammatory and immunomodulatory effects. Those compounds wherein R is H can be used to prepare the pharmacologically active derivatives.

  本发明涉及一种公式(I)CH3—(CH2)7—CH═CH—( )13—C(O)—O—( )3—OR的神经酸衍生物，其中R为氢（H）或羧酸残基；或化合物的盐，其中R为H；或其生物前体，前药。其中R为非H的化合物具有药理活性，特别是抗炎和免疫调节作用。其中R为H的化合物可用于制备药理活性衍生物。

表征谱图