硬脂酸 | 85541-42-0

• 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: 硬脂酸
• 中文别名: 十八烷-1-(13C)酸
• 英文名称: 1-[13C]-stearic acid
• 英文别名: [¹³C]stearic acid；stearic-1-13C acid；Stearic acid-1-13C；(113C)octadecanoic acid
• CAS: 85541-42-0
• 化学式: C₁₈H₃₆O₂
• mdl: MFCD00002753
• 分子量: 285.472
• InChiKey: QIQXTHQIDYTFRH-CPZJZEHKSA-N

物化性质

• 熔点：
  68-70 °C(lit.)
• 沸点：
  361 °C(lit.)
• 闪点：
  113℃
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• 稳定性/保质期：

  避免强氧化剂、强碱、强酸及强还原剂。

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.944
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Stearic acid-1-13C
CAS-No. : 85541-42-0
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)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
Precautionary statement(s) none
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R38 Irritating to skin.
S-phrase(s) none
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Octadecanoic acid-1-13C
Formula : 13CC17H36O2
Molecular Weight : 285,47 g/mol
Component Concentration
Stearic acid-1-13C
CAS-No. 85541-42-0 -

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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
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
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
no data available
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 dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
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.

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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.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Store under inert gas. hygroscopic
Specific end use(s)
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
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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 68 - 70 °C - lit.
point
f) Initial boiling point and 361 °C - lit.
boiling range
g) Flash point 113,00 °C - closed cup
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 1 hPa at 173,70 °C
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) Auto-ignition 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
Bases, Oxidizing agents, Reducing agents
Hazardous decomposition products
no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - > 2.000 mg/kg
Inhalation: no data available
LD50 Dermal - rabbit - > 5.000 mg/kg
LD50 Intravenous - rat - 21,5 mg/kg
Remarks: Behavioral:Convulsions or effect on seizure threshold. Lungs, Thorax, or Respiration:Other
changes.
no data available
Skin corrosion/irritation
Skin - rabbit - Skin irritation - 24,00 h
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
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.
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. 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.

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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

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  硬脂酸 在 硼烷四氢呋喃络合物 、 pyridinium dichlorochromate 、 aldehyde deformylating oxygenase 作用下， 以 四氢呋喃 、 二氯甲烷 、 甘油 为溶剂， 生成 正十七烷
  参考文献：
  名称：

  蓝藻醛脱羰酶仅将醛氧化裂解为烷基（a / e）酮和甲酸酯的证据

  摘要：

  蓝藻醛脱羰酶（ADs）催化C n脂肪醛向甲酸（HCO 2 –）和相应的C n -1链烷烃（a / e）的转化。以前对在大肠杆菌（Ec）中产生的点状点菜（Np）AD的研究表明，这种明显的水解反应实际上是一种隐秘的氧化还原氧合过程，其中一个O原子从O 2掺入甲酸酯中，然后进行基于蛋白质的还原系统（NADPH，铁氧还蛋白和铁氧还蛋白还原酶； N / F / FR）提供完全还原O 2所需的所有四个电子。马什及其同事随后发表的两篇论文[Das等。（2011）安格（Angew）。化学 诠释 埃德 50，7148-7152;Eser等。（2011）生物化学50，10743-10750]报道他们的Ec -expressed Np个和原绿球藻马里努斯（PM）AD制剂由O更快速地变换醛相同的产品2非依赖性的，真正的水解过程，这提示它们通过瞬时进行通过还原系统（必须使用化学系统，NADH和吩嗪硫酸甲酯； N /

  DOI：

  10.1021/bi300912n
• 作为产物：
  描述：

  十八烷酰氯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(邻甲基苯基)磷 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 18.0h， 生成 硬脂酸
  参考文献：
  名称：

  钯催化的脂肪族和苯甲酸氯化物的碳同位素交换

  摘要：

  提出了一种操作简单的钯催化 13CO 和 14CO 与活化脂肪族和苯甲羰基交换的协议。已经制备了几种 13C 和 14C 构建块、天然产物衍生物和药物，以展示后期碳同位素掺入的方法及其官能团兼容性。

  DOI：

  10.1021/jacs.8b09808

文献信息

• Unveiling the Structure and Reactivity of Fatty-Acid Based (Nano)materials Thanks to Efficient and Scalable ¹⁷O and ¹⁸O-Isotopic Labeling Schemes
  作者：Jessica Špačková、Charlyn Fabra、Sébastien Mittelette、Emeline Gaillard、Chia-Hsin Chen、Guillaume Cazals、Aurélien Lebrun、Saad Sene、Dorothée Berthomieu、Kuizhi Chen、Zhehong Gan、Christel Gervais、Thomas-Xavier Métro、Danielle Laurencin

  DOI：10.1021/jacs.0c09383

  日期：2020.12.16

  certain metal cations or materials surfaces. In this context, we have developed novel, efficient, user-friendly, and cost-effective synthetic protocols based on ball-milling, for the 17O and 18O isotopic labeling of two key fatty acids which are widely used in (nano)materials science, namely stearic and oleic acid. Labeled molecules were analyzed by 1H and 13C solution NMR, IR spectroscopy, and mass spectrometry

  脂肪酸在生物系统中无处不在，并广泛应用于材料科学，包括用于药物配方和纳米粒子的表面功能化。然而，有关这些分子的结构和反应性的重要问题仍有待阐明，包括它们与某些金属阳离子或材料表面的结合模式。在此背景下，我们开发了基于球磨的新颖、高效、用户友好且具有成本效益的合成方案，用于广泛应用于（纳米）材料科学的两种关键脂肪酸的 17O 和 18O 同位素标记，即硬脂酸和油酸。通过 1H 和 13C 溶液 NMR、IR 光谱和质谱（ESI-TOF 和 LC-MS）以及 17O 固态 NMR（针对 17O 标记物质）对标记分子进行分析。在这两种情况下，标记程序都扩大到在短短半天内生产出高达克数量的 17O 或 18O 富集分子，并且具有非常好的合成产率（全部≥84%）和富集水平（高达每个羧基氧平均为 46%）。然后，17O 标记的油酸用于合成金属皂（油酸锌）和 ZnO 纳米颗粒（NP）的表面功能化，首次通过高分辨率
• A metal-catalysed functional group metathesis approach to the carbon isotope labelling of carboxylic acids
  作者：R. Garrison Kinney、José Zgheib、Pierre-Louis Lagueux-Tremblay、Cuihan Zhou、Haifeng Yang、Jingwei Li、Donald R. Gauthier、Bruce A. Arndtsen

  DOI：10.1038/s41557-024-01447-7

  日期：2024.4

  describe an approach to directly carbon-label carboxylic-acid-containing pharmaceuticals via a metal-catalysed functional group exchange reaction, forming 14C-labelled carboxylic-acid-containing drugs without radioactive gases, in one pot, using an easily available and handled carboxylic acid 14C source. To enable this process, a functional group metathesis of carbon–carbon covalent bonds in acid chloride

  体内分子的分布、代谢和最终命运是药物活性的核心。然而，将放射性同位素引入药物上代谢稳定的碳位点以探测这些特征通常需要有毒的放射性气体，例如[ 14 C]CO和[ 14 C]CO 2 。在这里，我们描述了一种通过金属催化的官能团交换反应直接碳标记含羧酸药物的方法，使用一种容易获得的方法在一锅中形成14 C标记的含羧酸药物，无需放射性气体。处理羧酸14C源。为了实现这一过程，开发了酰基氯官能团中碳-碳共价键的官能团复分解，利用镍催化剂可逆地激活碳-氯键和有机分子之间交换官能团的能力。药物开发的适用性通过将14 C 标签或13 C 标签直接掺入一系列复杂的芳基、烷基、乙烯基和杂环羧酸药物或候选药物中来说明，无需气体或特殊设备，在环境条件下且无损失的放射性标记。
• The total synthesis of 2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine-1,3,1′-13C3 and -2,1′-13C2 by a novel chemoenzymatic method
  作者：Richard I. Duclos

  DOI：10.1016/j.chemphyslip.2009.08.001

  日期：2010.1

  2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A(2) was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydride. This phospholipid is an important biosynthetic precursor of arachidonic acid metabolites as well as the endocannabinoid 2-arachidonoylglycerol (2-AG), and is now available for NMR studies. (C) 2009 Elsevier Ireland Ltd. All rights reserved.
• US9673030B2
  申请人：——

  公开号：US9673030B2

  公开（公告）日：2017-06-06