岩皂甾醇 | 17605-67-3

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 岩皂甾醇
• 中文别名: 墨角藻甾醇；岩藻甾醇
• 英文名称: 28-Isofucosterol
• 英文别名: fucosterol；(3β,24E)-stigmasta-5,24(28)-dien-3-ol；(24E)-24-N-Propylidenecholesterol；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 17605-67-3
• 化学式: C₂₉H₄₈O
• 分子量: 412.7
• InChiKey: OSELKOCHBMDKEJ-JUGJNGJRSA-N

物化性质

• 熔点：
  118-120°C
• 比旋光度：
  D20 -38.4° (chloroform)
• 沸点：
  220-230 °C
• 密度：
  0.98±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）
• LogP：
  10.410 (est)
• 保留指数：
  3273.74;3305;3280;3305.7

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Fucosterol
CAS-No. : 17605-67-3
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
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: 5,24(28)-Stigmastadien-3β-ol
Synonyms
3β-Hydroxy-5,24(28)-stigmastadiene
Formula : C29H48O
Molecular Weight : 412,69 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
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.
Most important symptoms and effects, both acute and delayed
Some steroids show carcinogenic and teratogenic activity.
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
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
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
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
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
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. 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 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 acids, Strong bases
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
Some steroids show carcinogenic and teratogenic activity.
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
Some steroids show carcinogenic and teratogenic activity.
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. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
Some steroids show carcinogenic and teratogenic activity.
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

生物活性

Fucosterol 是一种甾醇，可以从藻类、海藻或硅藻中分离得到。它具有多种生物活性，包括抗氧化、抗脂肪生成、降低血液胆固醇水平、抗糖尿病和抗癌作用。Fucosterol 通过抑制 PPARα 和 C/EBPα 的表达来调控脂肪生成过程，并可用于抗肥胖试剂的研究开发。

靶点

Human Endogenous Metabolite

体外研究

Fucosterol（0-50 μM，7天）相较于完全分化的对照脂细胞抑制了 PPARα 和 C/EBPα 的表达。该化合物对 T47D 和 HT29 细胞系表现出细胞毒性，IC₅₀ 值分别为 27.94 和 70.41 μg/ml。同时，Fucosterol 还降低了 HEK293、MCF-7 和 SiHa 细胞的增殖，其 IC₅₀ 值分别为 185.4、43.3 和 34.0 μg/ml。

细胞系	浓度 (μM)	实验天数	结果
3T3-L1 脂肪细胞	0；25；50	7	抑制 PPARα 和 C/EBPα 表达

体内研究

口服给药（30 mg/kg）的 Fucosterol 显著降低了血清葡萄糖浓度，并抑制了晶状体中山梨醇的积累。

反应信息

• 作为反应物：
  描述：

  岩皂甾醇 在 对甲苯磺酰氯 作用下， 生成 3β-(toluene-4-sulfonyloxy)-stigmasta-5,24(28)c-diene
  参考文献：
  名称：

  Hey et al., Journal of the Chemical Society, 1950, p. 2881,2883

  摘要：

  DOI：
• 作为产物：
  描述：

  24-oxocholesterol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 岩皂甾醇
  参考文献：
  名称：

  合成模具von（24（28）E）-Stigmastadien-（5.24（28））-ol-（3β）和（24（28）E）-5α-Stigmastadien-（7.24（28））-ol-（3β）

  摘要：

  Die Titelverbindungen 1a和2a werden aus den 24-Oxo-sterinen 3和7 durch Reaktion mit Vinylmagnesiumbromid，Umsetzung der Vinylcarbinole 4b und 8b mit Phosphortrijodid unter Allylumlagerung zu den Allyljodiden und 6 und 9 und。Kleine Anteile der Z -konfigurierten Isomeren werden色谱分析von den Endprodukten缺失。

  DOI：

  10.1002/cber.19701030902

文献信息

• Novel sterol/stanol phosphorylnitroderivatives and use thereof in treating or preventing cardiovascular disease, its underlying conditions and other disorders
  申请人：Orchansky Liliana Patricia

  公开号：US20070232688A1

  公开（公告）日：2007-10-04

  Sterol and stanol phosphorylnitro derivatives and their use in treating or preventing cardiovascular disease, its underlying conditions and other disorders are disclosed. The disclosed compounds include a phosphate linker, at least one moiety that releases nitric oxide (NO), and a sterol or stanol moiety. Some compounds additionally include an ascorbyl moiety to make the compound more readily soluble in aqueous and non-aqueous media.

  甾醇和甾酚磷酸硝基衍生物及其在治疗或预防心血管疾病、其潜在病症和其他疾病中的用途被披露。所披露的化合物包括一个磷酸酯连接物、至少一个释放一氧化氮（NO）的基团，以及一个甾醇或甾酚基团。一些化合物还包括抗坏血酸基团，以使化合物在水性和非水性介质中更容易溶解。
• [EN] DERIVATIVES COMPRISING STEROLS AND/OR STANOLS AND SPECIFIC CLASSES OF ANTI-INFLAMMATORY AGENTS AND USE THEREOF IN TREATING OR PREVENTING CARDIOVASCULAR DISEASE<br/>[FR] DERIVES COMPRENANT DES STEROLS ET/OU DES STANOLS ET DES CLASSES SPECIFIQUES D'AGENTS ANTI-INFLAMMATOIRES, ET UTILISATION DESDITS DERIVES POUR LE TRAITEMENT OU LA PREVENTION DE MALADIES CARDIOVASCULAIRES
  申请人：FORBES MEDI TECH INC

  公开号：WO2004029068A1

  公开（公告）日：2004-04-08

  The present invention provides, in one aspect, novel derivatives comprising sterols and/or stanols and an NSAID selected from salicylic acids and arylalkanoic acids, including salts of these derivatives, and having one or more of the following formulae: a) R2-(CH2)n-CO-OR b) R2-R c) R2-CO-CO-OR d) formula (I), wherein R is a sterol or stanol moiety, R2 is derived from a salicylic acid or an arylalkanoic acid and n=1-5. Also provided are pharmaceutical compositions comprising one or more of these novel derivatives and methods of treating or preventing cardiovascular disease and its underlying conditions including, without limitation, atherosclerosis, hypercholesterolemia, hyperlipidemia, hypertension, thrombosis, coronary artery disease, and for treating and reducing inflammation including coronary plaque inflammation, bacterial-induced inflammation, viral induced inflammation and inflammation associated with acute pain and surgical procedures which comprises administering to an animal, particularly a human, a non-toxic and therapeutically effective amount of one or more of these compounds or a biologically acceptable salt thereof.

  本发明一方面提供了新颖的衍生物，包括甾醇和/或甾烷醇以及从水杨酸和芳烷酸中选择的非甾体抗炎药（NSAID），包括这些衍生物的盐，并具有以下一种或多种公式：a) R2-(CH2)n-CO-OR b) R2-R c) R2-CO-CO-OR d) 公式 (I)，其中R是甾醇或甾烷醇部分，R2来自水杨酸或芳烷酸，n=1-5。还提供了包含一种或多种这些新颖衍生物的药物组合物，以及治疗或预防心血管疾病及其基础条件的方法，包括但不限于动脉粥样硬化、高胆固醇血症、高脂血症、高血压、血栓形成、冠心病，以及治疗和减少炎症的方法，包括冠状动脉斑块炎症、细菌诱导的炎症、病毒诱导的炎症以及与急性疼痛和手术程序相关的炎症，该方法包括向动物，尤其是人类，投予一种或多种这些化合物或其生物学可接受的盐的非毒性和治疗有效量。
• LIPIDS, LIPID COMPOSITIONS, AND METHODS OF USING THEM
  申请人：BARYZA Jeremy

  公开号：US20110200582A1

  公开（公告）日：2011-08-18

  Disclosed are formulation and optimization protocols for delivery of therapeutically effective amounts of biologically active agents to liver, tumors, and/or other cells or tissues. Also provided are compositions and uses for cationic lipid compounds of formula (I). The invention also relates to compositions and uses for stealth lipids of formula (XI). Also provided are processes for making such compounds, compositions, and formulations, plus methods and uses of such compounds, compositions, and formulations to deliver biologically active agents to cells and/or tissues.

  本文披露了用于将生物活性剂量有效传递至肝脏、肿瘤和/或其他细胞或组织的配方和优化方案。还提供了具有化学式（I）的阳离子脂质化合物的组成和用途。该发明还涉及具有化学式（XI）的隐身脂质的组成和用途。还提供了制备这种化合物、组成物和配方的方法，以及利用这些化合物、组成物和配方将生物活性剂传递至细胞和/或组织的方法和用途。
• FORMULATIONS FOR THE DELIVERY OF ACTIVE AGENTS TO INSECTS, PLANTS, AND PLANT PATHOGENS
  申请人：Preceres Inc.

  公开号：US20170325457A1

  公开（公告）日：2017-11-16

  The present disclosure is directed to formulations comprising (1) at least one formulation transport agent, (2) at least one complexing agent, and (3) at least one active agent that modulates one or more traits of a target insect, plant, or plant pathogen. The present disclosure is also directed to methods of delivering such formulations to the target organism, as well as to formulation transport agents used to prepare such formulations.

  本公开涉及包含（1）至少一种制剂运输剂、（2）至少一种络合剂和（3）至少一种调节目标昆虫、植物或植物病原体的一个或多个特征的活性剂的配方。本公开还涉及将这种配方传递给目标生物体的方法，以及用于制备这种配方的制剂运输剂。
• Method for preparing analogue of vitamin D
  申请人：Ng Siong Chze

  公开号：US20070088007A1

  公开（公告）日：2007-04-19

  A method for preparing analogues of C1,C24-dihydroxy-vitamin D is disclosed. Especially the method for preparing calcipotriol and tacalcitol from a starting material of Vitamin D2 is disclosed here. Calcipotriol (compound 1(a)) and tacalcitol (compound 1(b)) can be synthesized by the method of the present invention. Moreover, only nine steps are needed for the synthesis of calcipotriol using the method. Likewise, only ten steps are needed for the synthesis of tacalcitol by the present method. Hence, the present method, with less process steps and higher yields, represents an improvement over the conventional methods.

  揭示了一种制备C1，C24-二羟基维生素D类似物的方法。特别是在这里揭示了从维生素D2起始物质制备钙醇和他卡尔西醇的方法。钙醇（化合物1(a)）和他卡尔西醇（化合物1(b)）可以通过本发明的方法合成。此外，使用该方法合成钙醇只需要九个步骤。同样，使用本方法合成他卡尔西醇只需要十个步骤。因此，本方法具有更少的工艺步骤和更高的产量，相对于传统方法而言，代表了一种改进。