(3A,5R,6B)-6-甲氧基-3,5-环胆甾烷 | 2867-93-8

• 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: (3A,5R,6B)-6-甲氧基-3,5-环胆甾烷
• 英文名称: 6β-methoxy-3α,5-cyclocholestane
• 英文别名: 6β-methoxy-3α,5-cyclo-5-α-cholestane；6β-methoxy-3α,5α-cyclocholestane；6β-Methoxy-3α,5-cyclo-5α-cholestan；Isocholesterylmethylaether；epi-cholesteryl methyl ether；i-Cholesterol methyl ether；(1S,2R,5R,7R,8R,10S,11S,14R,15R)-8-methoxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]pentacyclo[8.7.0.02,7.05,7.011,15]heptadecane
• CAS: 2867-93-8
• 化学式: C₂₈H₄₈O
• 分子量: 400.689
• InChiKey: DSVYQBSADVVKNY-HHZNOXSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : i-Cholesteryl methyl ether
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 2867-93-8
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
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
: 6β-Methoxy-3α,5-cyclocholestane
Synonyms
3α,5-Cyclo-5α-cholestan-6β-ol methyl ether
Formula : C28H48O
Molecular Weight : 400,68 g/mol
CAS-No. : 2867-93-8
No components need to be disclosed according to the applicable regulations.

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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 vapours, mist or gas.
For personal protection see section 8.
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.
For precautions see section 2.2.
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: -20 °C
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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).
Control of environmental exposure
Do not let product enter drains.

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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 77 - 79 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration 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) 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
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
LD50 Intravenous - mouse - 180 mg/kg
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

异胆甾醇甲醚是用于生命科学研究的一种生物化学试剂，可以作为生物材料或有机化合物使用。

反应信息

• 作为反应物：
  描述：

  (3A,5R,6B)-6-甲氧基-3,5-环胆甾烷 在 水 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以20 mg的产率得到胆固醇
  参考文献：
  名称：

  isofucosterol在生物合成期间羊毛甾醇的异亚丙基甲基的立体化学命运松pinea

  摘要：

  [26- 3 H]羊毛甾醇（16）中的溶液施用至松pinea和[26- 3 H]乙酸isofucosteryl（6）中得到的化学转化成[26- 3 H]胆固醇（13）。将化合物（13）与大鼠肝线粒体一起温育以产生[3- 3 H]丙酸。获得的数据是具有生物合成途径相一致，其中所述亲的Δ的-E异亚甲基24 -precursor变为亲-R异丙基甲基组中isofucosterol。

  DOI：

  10.1039/p19810000498
• 作为产物：
  描述：

  4-methylpentyllithium 在 palladium-barium carbonate 氢气 、 copper(l) cyanide 作用下， 以 乙酸乙酯 为溶剂， -30.0~-23.0 ℃ 、310.27 kPa 条件下， 反应 33.67h， 生成 (3A,5R,6B)-6-甲氧基-3,5-环胆甾烷
  参考文献：
  名称：

  Organocuprate-mediated methods for the stereospecific introduction of steroid side chains at C-20

  摘要：

  DOI：

  10.1021/jo00157a002

文献信息

• 3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates
  作者：Aneta M Tomkiel、Adam Biedrzycki、Jolanta Płoszyńska、Dorota Naróg、Andrzej Sobkowiak、Jacek W Morzycki

  DOI：10.3762/bjoc.11.16

  日期：——

  3α,5α-Cyclocholestan-6β-yl alkyl and aryl ethers were proved to be efficient cholesteryl donors in the electrochemical synthesis of glycoconjugates. 3α,5α-Cyclocholestan-6β-ol (i-cholesterol) and its tert-butyldimethylsilyl ether can also be used for this purpose. The i-cholesterol derivatives show similar reactivities to those of previously studied 3α,5α-cyclocholestan-6β-thioethers.

  3α,5α-环胆甾烷-6β-基烷基和芳基醚被证明是在糖脂共轭物的电化学合成中高效的胆固醇供体。3α,5α-环胆甾烷-6β-醇（i-胆固醇）及其tert-丁基二甲基硅醚也可用于此目的。i-胆固醇衍生物显示出与先前研究的3α,5α-环胆甾烷-6β-硫醚类似的反应性。
• Der dipolar aprotisch-protische Lösungsmitteleffekt bei der nucleophilen Substitution des Cholesteryltosylats
  作者：Alfred Bertho

  DOI：10.1002/jlac.19687140116

  日期：1968.7.23

  Die nucleophile Substitution des Cholesteryltosylats (1) durch die Nucleophile N3⊖, SCN⊖, Br⊖, J⊖ und Dimethylamin in protischen und aprotischen Medien wird untersucht. Der aprotisch-protische Effekt wird bei N3⊖ und SCN⊖ beobachtet; er ist bei Dimethylamin wahrscheinlich, fehlt aber bei Br⊖ und J⊖. – Unter den Nebenprodukten der Substitution finden sich Steroid-Verbindungen (Tabb. 1–5 ), die zum Teil

  胆甾醇的亲核取代甲苯磺酸酯（1）通过亲核试剂Ñ 3 ⊖，SCN ⊖，溴⊖，J ⊖和在质子和非质子媒体二甲胺进行了研究。非质子-质子作用与N-观察到3 ⊖和SCN ⊖ ; 它很可能为二甲胺，但缺少溴⊖和J ⊖。-取代的副产物包括类固醇化合物（表1-5），其中一些以新的形成形式出现。-将结果与有关阴离子的可溶性和非质子溶剂对阳离子的可溶性的信息进行比较。
• [EN] SYNTHESIS OF CHOLESTEROL AND VITAMIN D3 FROM PHYTOSTEROLS<br/>[FR] SYNTHÈSE DE CHOLESTÉROL ET DE VITAMINE D3 À PARTIR DE PHYTOSTÉROLS
  申请人：FERMENTA BIOTECH LTD

  公开号：WO2021005618A1

  公开（公告）日：2021-01-14

  The present invention discloses novel method for synthesizing vegan cholesterol and vitamin D3 from inexpensive crude phytosterol.

  本发明揭示了一种从廉价的粗植物甾醇中合成素食胆固醇和维生素D3的新方法。
• 291. A modified procedure for the preparation of 3,5-cyclosteroids
  作者：M. S. Patel、W. J. Peal

  DOI：10.1039/jr9630001544

  日期：——
• Organocuprate-mediated methods for the stereospecific introduction of steroid side chains at C-20
  作者：Norman R. Schmuff、Barry M. Trost

  DOI：10.1021/jo00157a002

  日期：1983.5