cholestan-3-one | 566-88-1

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 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
• 英文名称: cholestan-3-one
• 英文别名: (5α)-cholestan-3-one；5α-Cholestan-3-on；5β-Cholestan-3-on；Cholestan-3-on；3-Cholestanon；Cholestanon-3；10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 566-88-1；601-53-6；14615-13-5；14733-20-1；15600-08-5；80629-93-2
• 化学式: C₂₇H₄₆O
• 分子量: 386.662
• InChiKey: PESKGJQREUXSRR-UHFFFAOYSA-N

物化性质

• 熔点：
  128-133 °C
• 比旋光度：
  [α]D20 +40～+44° (c=1, CHCl3)
• 沸点：
  452.9±13.0 °C(Predicted)
• 密度：
  0.953
• 溶解度：
  可溶于氯仿（少量）
• 碰撞截面：
  187.2 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
• 保留指数：
  3145
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 储存条件：
  贮存： 将密器密封后，储存在密封的主要容器中，并置于阴凉、干燥处。

SDS

Name:	5-alpha-Cholestan-3-one 97% Material Safety Data Sheet
Synonym:	None
CAS:	15600-08-5

Section 1 - Chemical Product MSDS Name:5-alpha-Cholestan-3-one 97% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15600-08-5	5-alpha-Cholestan-3-one, 97%	97%	239-682-1

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid if cough or other symptoms appear.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Wash hands before eating. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas.
Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Good general ventilation should be sufficient to control airborne levels.
Exposure Limits CAS# 15600-08-5: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 128 - 130 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C27H46O
Molecular Weight: 386.65

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidants.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 15600-08-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-alpha-Cholestan-3-one, 97% - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 15600-08-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 15600-08-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15600-08-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性的化合物 5α-Cholestan-3-one 是一种内源性代谢产物。

反应信息

• 作为反应物：
  描述：

  cholestan-3-one 、 3,5-dimethoxysalicylic alcohol 在 phosphorus pentoxide 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以93%的产率得到6',8'-dimethoxy-10,13-dimethyl-17-(6-methylheptan-2-yl)spiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,2'-4H-1,3-benzodioxine]
  参考文献：
  名称：

  激发态元效应在光不稳定保护基设计中的应用。

  摘要：

  基于激发态的间位效应，已经开发了一种新型的羰基化合物的光不稳定保护基。

  DOI：

  10.1021/ol071085c
• 作为产物：
  描述：

  Cholestanol 在 palladium diacetate 吡啶 、 氧气 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以92%的产率得到cholestan-3-one
  参考文献：
  名称：

  钯（II）分子氧催化醇氧化为醛和酮。

  摘要：

  Pd（OAc）（2）/吡啶/ MS3A的新颖组合可将甲苯中的各种伯醇和仲醇中的好氧氧化催化高产率地转化为相应的醛和酮。各种取代基和保护基与该氧化相容。该ca。观察到O（2）吸收与产物收率的2：3比率，而在没有MS3A的情况下，该比率为ca。1：1，表明H（2）O（2）的原位形成及其通过MS3A分解为水和氧气的过程。提出了一种催化循环，包括形成Pd（II）-醇盐，然后β-消除Pd（II）H物质和羰基化合物，然后形成Pd（II）OOH物质。

  DOI：

  10.1021/jo9906734

文献信息

• Obsevations on the cleavage of the bismuth–carbon bond in Bi^Vcompounds: a new arylation reaction
  作者：Derek H. R. Barton、David J. Lester、William B. Motherwell、M. Teresa Barros Papoula

  DOI：10.1039/c39800000246

  日期：——

  trianyl-organobismuth oxidants are presented; deuterium labelling studies have established that the mechanism of oxidation of allylic alcohols by these reagents involves, to some extent, cleavage of the bismuth–aryl bond; several reactions involving the synthetically useful transfer of an aryl group from bismuth to nitrogen and to carbon are described.

  给出了五价三芳基-有机铋氧化剂的选择性的其他实例；参见表1。氘标记研究已经确定，这些试剂氧化烯丙醇的机理在一定程度上涉及铋-芳基键的裂解。描述了涉及芳基从铋到氮和碳的合成上有用的转移的几种反应。
• GAGLIOTI L.; GASPARRINI F.; MISITI D.; PALMIERI G., SYNTHESIS, 1979, NO 3, 207-208
  作者：GAGLIOTI L.、 GASPARRINI F.、 MISITI D.、 PALMIERI G.

  DOI：——

  日期：——
• GALLOIS PH.; BRUNET J.-J.; CAUBERE P., J. ORG. CHEM , 1980, 45, NO 10, 1946-1950
  作者：GALLOIS PH.、 BRUNET J.-J.、 CAUBERE P.

  DOI：——

  日期：——
• MITSUNOBU OYO; YOSHIDA NAOYUKI, TETRAHEDRON LETT., 1981, 22, NO 24, 2295-2296
  作者：MITSUNOBU OYO、 YOSHIDA NAOYUKI

  DOI：——

  日期：——
• Steroid derivatives of fullerenes
  申请人：MacFarland Darren

  公开号：US20080214514A1

  公开（公告）日：2008-09-04

  Described herein are steroid derivatives of fullerene moieties, for example fullerene derivatives in which cholesterol, or a cholesterol moiety, is attached via ester, amide, or ether bonds to one of a variety of “linkers,” e.g., chemical groups including alkyl chains and aromatic groups, which are then connected to the fullerene moiety. The steroid moiety can confers useful solubility in components of biological fluids and/or pharmacologically acceptable carriers and can also affect the biodistribution of the fullerenes which makes the derivatives useful in imaging, diagnosis and the treatment or management of disease or complications of disease states.