硬脂酸缩水甘油基酯 | 7460-84-6

• 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: 硬脂酸缩水甘油基酯
• 中文别名: 缩水甘油酯硬脂酸
• 英文名称: glycidyl octadecanoyl ether
• 英文别名: stearic acid glycidyl ester；2,3-epoxypropyl stearate；glycidol stearate；glycidyl stearate；glycidol sterate；octadecanoyloxymethyl-oxirane；oxiran-2-ylmethyl octadecanoate
• CAS: 7460-84-6
• 化学式: C₂₁H₄₀O₃
• mdl: MFCD00059110
• 分子量: 340.547
• InChiKey: OUQGOXCIUOCDNN-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  193 °C / 1mmHg
• 密度：
  1.0240 (rough estimate)
• 溶解度：
  氯仿（少量溶解）、乙酸乙酯（少量，超声处理）、己烷（少量，加热）
• 稳定性/保质期：
  如果遵照规格使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  24
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.952
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

毒理性

• 致癌物分类

国际癌症研究机构致癌物：缩水甘油硬脂酸酯

IARC Carcinogenic Agent:Glycidyl stearate

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专论集：第11卷（1976年）：镉、镍、一些环氧化合物、其他工业化学品及对挥发性麻醉剂的总体考虑

IARC Monographs:Volume 11: (1976) Cadmium, Nickel, Some Epoxides, Miscellaneous Industrial Chemicals and General Considerations on Volatile Anaesthetics

来源:International Agency for Research on Cancer (IARC)

安全信息

• RTECS号：
  WI3500000
• 海关编码：
  2915709000
• 储存条件：
  密封在阴凉干燥的环境中。

SDS

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Section I.Chemical Product and Company Identification
Chemical Name Stearic Acid Glycidyl Ester
Portland OR
Synonym 2,3-Epoxy-1-propanol Stearate
Chemical Formula C17H35COOCH2C2H3O
CAS Number 7460-84-6

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
Stearic Acid Glycidyl Ester 7460-84-6 ------------- This chemical is classified as Not available.
a possible carcinogen. There
is no acceptable exposure limit
for a carcinogen.

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Section III. Hazards Identification
Acute Health Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Possible carcinogen.
(sufficient evidence in animals, no adaquate data in humans)
Tumorigenic: Rat (subcutaneous) 2500 mg/kg/5W-I. Equivocal tumorigenic by RTECS criteria.
Tumorigenic: Mouse (subcutaneous) 52 mg/kg/26W-I. Equivocal tumorigenic by RTECS criteria.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. DO NOT use an eye ointment. Flush eyes with running water for a minimum
of 15 minutes, occasionally lifting the upper and lower eyelids. Seek medical attention. Treat symptomatically and
supportively.
Skin Contact After contact with skin, wash immediately with plenty of water. Gently and thoroughly wash the contaminated skin with
running water and non-abrasive soap. Be particularly careful to clean folds, crevices, creases and groin. Cover the
irritated skin with an emollient. Seek medical attention. Treat symptomatically and supportively. Wash any contaminated
clothing before reusing.
Inhalation If the victim is not breathing, perform artificial respiration. Loosen tight clothing such as a collar, tie, belt or waistband. If
breathing is difficult, oxygen can be administered. Seek medical attention. Treat symptomatically and supportively.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt, or waistband. If the victim is not breathing, administer artificial respiration.
Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic material
was ingested; the absence of such signs, however, is not conclusive. Seek immediate medical attention and, if possible,
show the chemical label. Treat symptomatically and supportively.

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Section V. Fire and Explosion Data
Not available.
Flammability Combustible. Auto-Ignition
Flash Points Flammable Limits
Not available. Not available.
Combustion Products
These products are toxic carbon oxides (CO, CO 2).
Fire Hazards
No specific information is available regarding the flammability of this compound in the presence of various materials.
Explosion Hazards Risks of explosion of the product in presence of mechanical impact: Not available.
Risks of explosion of the product in presence of static discharge: Not available.
No additional information is available regarding the risks of explosion.
Continued on Next Page
Stearic Acid Glycidyl Ester
Fire Fighting Media
SMALL FIRE: Use DRY chemicals, CO 2, water spray or foam.
and Instructions LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.

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Section VI. Accidental Release Measures
Spill Cleanup Harmful material.
Instructions In case of a spill and/or a leak, always shut off any sources of ignition, ventilate the area, and exercise caution. Use a
shovel to put the material into a convenient waste disposal container. Finish cleaning the spill by rinsing any
contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
disposal.

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Section VII. Handling and Storage
POSSIBLE CARCINOGEN. Keep away from heat and sources of ignition. Mechanical exhaust required. When not in
Handling and Storage
use, tightly seal the container and store in a dry, cool place. Avoid excessive heat and light. DO NOT breathe dust. In
Information
case of insufficient ventilation, wear suitable respiratory equipment. If you feel unwell, seek medical attention and show
the label when possible. Treat symptomatically and supportively. Avoid contact with skin and eyes.
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection Splash goggles. Lab coat. Dust respirator. Boots. Gloves. A MSHA/NIOSH approved respirator must be used to avoid
inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE handling
this product.
Exposure Limits This chemical is classified as a possible carcinogen. There is no acceptable exposure limit for a carcinogen.

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Section IX. Physical and Chemical Properties
Physical state @ 20°C White crystalline powder. Solubility
Not available.
Not available.
Specific Gravity
Molecular Weight 340.55 Partition Coefficient
Not available.
Boiling Point Vapor Pressure
Not available. Not available.
51 to 53°C (123.8 to 127.4°F) Not available.
Melting Point Vapor Density
Refractive Index Not available. Volatility Not available.
Critical Temperature Not available. Odor Not available.
Viscosity Not available. Taste Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability
Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents.

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Section XI. Toxicological Information
RTECS Number WI3500000
Routes of Exposure Eye contact. Inhalation. Ingestion.
Toxicity Data Not available.
CARCINOGENIC EFFECTS : Possible carcinogen.
Chronic Toxic Effects
(sufficient evidence in animals, no adaquate data in humans)
Tumorigenic: Rat (subcutaneous) 2500 mg/kg/5W-I. Equivocal tumorigenic by RTECS criteria.
Tumorigenic: Mouse (subcutaneous) 52 mg/kg/26W-I. Equivocal tumorigenic by RTECS criteria.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Acute Toxic Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
Continued on Next Page
Stearic Acid Glycidyl Ester

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Section XII. Ecological Information
Ecotoxicity Not available.
Environmental Fate Not available.

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local or regional authorities. You may be able to dissolve or mix material with
Waste Disposal
a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state, and local regulations when disposing of this substance.

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Section XIV. Transport Information
DOT Classification Not a DOT controlled material (United States).
PIN Number Not applicable.
Proper Shipping Name
Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not controlled under WHMIS (Canada).
(Canada)
EINECS Number (EEC) Not available.
EEC Risk Statements Not available.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

药物成分（用于钙信号研究）

反应信息

• 作为反应物：
  描述：

  硬脂酸缩水甘油基酯 在 吡啶 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.83h， 生成
  参考文献：
  名称：

  Efficient synthesis of 3-O-thia-cPA and preliminary analysis of its biological activity toward autotaxin

  摘要：

  The efficient synthesis of 3-O-thia-cPAs (4a-d), sulfur analogues of cyclic phosphatidic acid (cPA), has been achieved. The key step of the synthesis is an intramolecular Arbuzov reaction to construct the cyclic thiophosphate moiety. The present synthetic route enables the synthesis of 4a-d in only four steps from the commercially available glycidol. Preliminary biological experiments showed that 4a-d exhibited a similar inhibitory effect on autotaxin (ATX) as original cPA. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.083
• 作为产物：
  描述：

  硬脂酸烯丙酯 生成 硬脂酸缩水甘油基酯
  参考文献：
  名称：

  Vegetable based dioxanone derivatives, synthesis and uses thereof

  摘要：

  本发明涉及连接到长度在2到24碳之间的碳链上的羧酸和酯基团，其中该链含有至少一个二氧杂环己酮环系统，所述二氧杂环己酮是由链中的两个相邻碳和/或链中的至少一个碳被取代为挂链的二氧杂环己酮环系统而形成的。在优选实施例中，碳链是脂肪酸残基。所述链的碳可以选择性地被取代、饱和或不饱和。当存在两个或更多的酯基团时，该发明涉及一种聚酯，例如三酸甘油酯，其中包含多个碳链，每个链都独立地衍生，使得三酸甘油酯含有至少一个二氧杂环己酮环系统，所述二氧杂环己酮是由至少一个链中的两个相邻碳形成的。本发明还涉及制备含有二氧杂环己酮的组合物或脂肪酸衍生物的方法。本发明还涉及利用含有二氧杂环己酮的组合物或脂肪酸衍生物的涂料配方和聚合物，以及制备此类涂料和聚合物的方法。

  公开号：

  US20050234121A1

文献信息

• Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties
  作者：Vladimir F. Mironov、Andrey V. Nemtarev、Olga V. Tsepaeva、Mudaris N. Dimukhametov、Igor A. Litvinov、Alexandra D. Voloshina、Tatiana N. Pashirova、Eugenii A. Titov、Anna P. Lyubina、Syumbelya K. Amerhanova、Aidar T. Gubaidullin、Daut R. Islamov

  DOI：10.3390/molecules26216350

  日期：——

  of (2-hydroxypropyl)triphenylphosphonium triflates 3 substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride etherate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium

  已证明，对于多种环氧化合物，它们与三氟甲磺酸三苯基鏻的相互作用具有高化学选择性，并导致形成 3-位被烷氧基、烷基羧基取代的 (2-羟丙基)三苯基鏻三氟甲磺酸盐3卤素，以高产率分离。采用在三氟化硼乙醚合物存在下环氧氯丙烷与醇反应的方法，然后用碘取代氯并用三苯基膦处理，也得到2-羟丙基三苯基碘化鏻4 。建立了所获得的鏻盐的分子和超分子结构，并揭示了它们与十二指肠腺癌相关的高抗肿瘤活性。基于鏻盐3和L -α-磷脂酰胆碱(PC)的脂质体系统的形成用于提高生物利用度并降低毒性。它们是通过薄膜再水化方法生产的，并表现出细胞毒性特性。鏻盐3和4的合理设计具有作为靶向递送至肿瘤细胞线粒体的新载体的巨大潜力。
• Synthesis of triglycerides from 1,3-dibromopropan-2-ol
  作者：Asharam Bhati、Richard J. Hamilton、David A. Steven、Rajender Aneja、Frederick B. Padley

  DOI：10.1039/p29830001553

  日期：——

  1,3-Dibromopropan-2-ol (I) was converted into an acyl derivative (VI) by reaction with an appropriate acyl chloride in the presence of pyridine. The acyl derivative (VI) was subjected to nucleophilic substitution with 3 mol. equiv. tris(decyl)methylammonium carboxylate in refluxing hexane. This led to symmetrical diacid triglycerides in 90–94% yield. Substitution with an equimolar amount of the carboxylate

  通过在吡啶存在下与适当的酰氯反应，将1，3-二溴丙烷-2-醇（I）转化为酰基衍生物（VI）。对酰基衍生物（VI）进行3摩尔亲核取代。当量 在回流己烷中的羧酸三（癸基）甲基铵。这导致对称的二酸甘油三酯收率达到90-94％。用等摩尔量的羧酸取代，主要提供1,2-双酰氧基-3-溴丙烷（VII），可以轻松地将其分离并进一步取代，从而得到约不对称的二酸和三酸三甘油酯。产率96％。脂解显示合成的甘油三酸酯为约。纯度为99％。
• COMPOSITIONS COMPRISING ALKOXYSILANE-CONTAINING ISOCYANATES AND ACID STABILISERS
  申请人：SPYROU Emmanouil

  公开号：US20150274760A1

  公开（公告）日：2015-10-01

  The present invention relates to a composition comprising (A) an isocyanate of formula (I) OCN-A-SiR 1 R 2 R 3 (I), wherein A is straight-chain, branched, substituted and/or unsubstituted aliphatic hydrocarbyl of 1 to 12 carbon atoms or substituted or unsubstituted cycloaliphatic hydrocarbyl of 4 to 18 carbon atoms, wherein R 1 is selected from the group comprising —O—R alk , wherein R 2 and R 3 are each independently selected from the group of substituents comprising —R alk and —O—R alk , and wherein —R alk is hydrocarbyl of 1 to 6 carbon atoms, and B) a Bronstedt or Lewis acid or a compound which releases a Bronstedt or Lewis acid at room temperature; and also to a process for producing a stabilized alkoxysilane-containing isocyanate comprising the step of adding a Lewis or Bronstedt acid or a compound which releases a Bronstedt or Lewis acid at room temperature to an alkoxysilane-containing isocyanate.

  本发明涉及一种组合物，包括（A）式（I）OCN-A-SiR1R2R3（I）的异氰酸酯，其中A是1至12个碳原子的直链、支链、取代和/或未取代的脂肪烃基或4至18个碳原子的取代或未取代的环脂肪烃基，其中R1选自包括-O-Ralk的基团，其中R2和R3各自独立地选自包括-Ralk和-O-Ralk的取代基团的群，其中-Ralk是1至6个碳原子的烃基，以及（B）布朗斯特或路易斯酸或在室温下释放布朗斯特或路易斯酸的化合物；还涉及一种生产稳定的含烷氧基硅烷的异氰酸酯的方法，该方法包括向含烷氧基硅烷的异氰酸酯中加入路易斯或布朗斯特酸或在室温下释放布朗斯特或路易斯酸的化合物的步骤。
• 一种脂肪酸二聚甘油酯及其制备方法和应用
  申请人：南京林业大学

  公开号：CN113896636A

  公开（公告）日：2022-01-07

  本发明属于有机化工技术领域，提供了一种脂肪酸二聚甘油酯及其制备方法和应用。本发明提供了一种脂肪酸二聚甘油酯，具有式I所述结构：式I中，R为烷烃基或烯烃基；所述烷烃基为C11‑C17烷烃基；所述烯烃基为C11‑C17烯烃基。在本发明中，由于式I中，R为碳链很长的基团，使得脂肪酸二聚甘油酯沸点高且耐热性好。同时，由于脂肪酸二聚甘油酯含有三个羟基，使得脂肪酸二聚甘油酯作为纸张柔软保湿剂时，具有较好的锁水保湿及柔软性能。
• Polyether-polyol compound
  申请人：——

  公开号：US20020035238A1

  公开（公告）日：2002-03-21

  A polyether-polyol compound represented by the compositional formula C 3n H 6n+2 O 2n+1 , wherein n is an integer of 4 or more, wherein the polyether-polyol compound has a total number of 1,2-diol unit and 1,3-diol unit of [(n/2)+1] in a case where n is an even number of 4 or more, or a total number of 1,2-diol unit and 1,3-diol unit of [((n−1)/2)+1] and one hydroxyl group which is not involved in the units in a case where n is an odd number of 5 or more; a polyglycerol alkyl ether, a part of hydroxyl groups in a polyglycerol being substituted by an alkyl group, wherein the polyglycerol is the polyether polyol compound mentioned above; and an ester prepared by the process comprising reacting the polyether-polyol compound mentioned above or the polyglycerol alkyl ether mentioned above with a fatty acid.

  一种由组成式C3nH6n+2O2n+1表示的聚醚聚醇化合物，其中n是4或更大的整数，在n为4或更大的偶数时，聚醚聚醇化合物具有[(n/2)+1]个1,2-二醇基和1,3-二醇基的总数，在n为5或更大的奇数时，聚醚聚醇化合物具有[((n−1)/2)+1]个1,2-二醇基和1,3-二醇基的总数以及一个未参与上述单元的羟基；一种聚甘油烷基醚，其中聚甘油是上述聚醚聚醇化合物，其部分羟基被烷基取代；以及通过将上述聚醚聚醇化合物或上述聚甘油烷基醚与脂肪酸反应制备的酯。

表征谱图