(20S)-20-(hydroxymethyl)pregna-1,4-dien-3-one | 35525-27-0

• 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: (20S)-20-(hydroxymethyl)pregna-1,4-dien-3-one
• 英文别名: 22-hydroxy-23,24-bis-norchola-1,4-diene-3-one；(20S)-20-hydroxymethylpregna-1,4-dien-3-one；(20S)-20-Hydroxymethylpregna-1,4-dien-3-on；22-hydroxy-23,24-bisnorchol-1,4-dien-3-one；ZK18364；(20S)-21-hydroxy-20-methyl-pregna-1,4-dien-3-one；(8S,9S,10R,13S,14S,17R)-17-[(2S)-1-hydroxypropan-2-yl]-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 35525-27-0
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: FRCNDHZJYALSFS-HOFZUOGSSA-N

物化性质

• 熔点：
  178-184 °C
• 沸点：
  406.22°C (rough estimate)
• 密度：
  1.0474 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25

SDS

Name:	20-(Hydroxymethyl)pregna-1 4-dien-3-one 95% Material Safety Data Sheet
Synonym:	None
CAS:	35525-27-0

Section 1 - Chemical Product MSDS Name:20-(Hydroxymethyl)pregna-1 4-dien-3-one 95% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
35525-27-0	20-(Hydroxymethyl)pregna-1,4-dien-3-on	95	unlisted

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. May be harmful if absorbed through the skin. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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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. Dusts at sufficient concentrations can form explosive mixtures with air. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use extinguishing media most appropriate for the surrounding fire.

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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. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.
Hormones and antibiotics room.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 35525-27-0: 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 minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: cream to white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 180.00 - 181.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C22H32O2
Molecular Weight: 328.48

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 35525-27-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
20-(Hydroxymethyl)pregna-1,4-dien-3-one - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 35525-27-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 35525-27-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 35525-27-0 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

反应信息

• 作为反应物：
  描述：

  (20S)-20-(hydroxymethyl)pregna-1,4-dien-3-one 在 2,4,6-三甲基吡啶 、 甲醇 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 双氧水 、 lithium 、 氯化铵 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 、 四氯化碳 、 乙醇 、 甲苯 为溶剂， 反应 29.25h， 生成 (20S)-21-(1-Aethoxyaethoxy)-20-methyl-5-pregnen-1α,3β-diol
  参考文献：
  名称：

  EINE ergiebige Herstellung冯1α，3β二羟基Δ 5 -steroiden第三人以Reduktion冯1α，2α环氧-4,6-二烯-3- onen MIT锂在Ammoniak †

  摘要：

  用于制备1α，3β二羟基Δ的有效程序5个由1α还原，-steroids2α环氧-4,6-二烯-3-酮与锂在氨

  DOI：

  10.1002/hlca.19810640621
• 作为产物：
  描述：

  bisnoralcohol 在 4-二甲氨基吡啶 、 二苯基二硒醚 、 三乙胺 、 1-羟基-1,3-二氧代-1lambda5,2-苯并碘氧戊环-4-羧酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.75h， 生成 (20S)-20-(hydroxymethyl)pregna-1,4-dien-3-one
  参考文献：
  名称：

  Biocatalytic Steroidal 9α‐Hydroxylation and Fragmentation Enable the Concise Chemoenzymatic Synthesis of 9,10‐Secosteroids

  摘要：

  9,10‐Secosteroids are an important group of marine steroids with diverse biological activities. Herein, we report a chemoenzymatic strategy for the concise, modular, and scalable synthesis of ten naturally occurring 9,10‐secosteroids from readily available steroids in three to eight steps. The key feature lies in utilizing a Rieske oxygenase‐like 3‐ketosteroid 9α‐hydroxylase (KSH) as the biocatalyst to achieve efficient C9−C10 bond cleavage and A‐ring aromatization of tetracyclic steroids through 9α‐hydroxylation and fragmentation. With synthesized 9,10‐secosteroides, structure–activity relationship was evaluated based on bioassays in terms of previously unexplored anti‐infective activity. This study provides experimental evidence to support the hypothesis that the biosynthetic pathway through which 9,10‐secosteroids are formed in nature shares a similar 9α‐hydroxylation and fragmentation cascade. In addition to the development of a biomimetic approach for 9,10‐secosteroid synthesis, this study highlights the great potential of chemoenzymatic strategies in chemical synthesis.

  DOI：

  10.1002/anie.202319624

文献信息

• The CuI-catalyzed alkyne–azide cycloaddition as direct conjugation/cyclization method of peptides to steroids
  作者：Radell Echemendía、Odette Concepción、Fidel E. Morales、Márcio W. Paixão、Daniel G. Rivera

  DOI：10.1016/j.tet.2013.10.032

  日期：2014.5

  good to excellent yields. The process comprised the solution-phase synthesis of oligopeptides featuring varied chain length and amino acid sequence as well as the preparation of a small library of azidosteroids bearing the azido group either at the side chain or the steroidal nucleus. An alternative strategy relying on a sequential peptide coupling/CuAAC-based macrocyclization procedure was also developed

  铜我催化的叠氮化物-炔烃1,3-偶极环加成反应是炔基肽与叠氮类固醇的直接缀合方法，从而能够以优异的产率制备新型的三唑连接的肽-类固醇缀合物。该方法包括溶液相合成具有变化链长和氨基酸序列的寡肽，以及制备在侧链或甾体核上带有叠氮基的小叠氮类固醇文库。还开发了一种基于顺序肽偶联/基于CuAAC的大环化程序的替代策略，以提供具有不同大小和拓扑结构的大环肽-类固醇共轭物。两种方法均显示出很高的化学效率和多功能性，
• Isolation, Biological Significance, Synthesis, and Cytotoxic Evaluation of New Natural Parathiosteroids A−C and Analogues from the Soft Coral <i>Paragorgia</i> sp.
  作者：Javier Jesús Poza、Rogelio Fernández、Fernando Reyes、Jaime Rodríguez、Carlos Jiménez

  DOI：10.1021/jo801198u

  日期：2008.10.17

  Three unusual new steroid thioesters, parathiosteroids A-C (1a-3a), were isolated from the 2-propanol extract of the soft coral Paragorgia sp. collected in Madagascar. Their structures, determined by detailed spectroscopic analysis, were confirmed by synthesis and represent the first isolation of natural steroids bearing a C22 thioester in their side chain. These compounds displayed cytotoxicity against

  从软珊瑚Paragorgia sp。的2-丙醇提取物中分离出三种不同寻常的新类固醇硫酯，对硫类固醇AC（1a-3a）。收集在马达加斯加。通过详细的光谱分析确定的结构，通过合成得到证实，代表了其侧链带有C22硫酯的天然类固醇的首次分离。这些化合物在微摩尔水平上对一组三个人类肿瘤细胞系显示出细胞毒性。几种类似物的制备揭示了这种类固醇的结构/活性关系，例如，侧链中的XCH2CH2NHCOCH3部分（X = S，O，NH）对于抗增殖活性是必不可少的，并且在氧化过程中氧化程度低A环可提高生物活性。
• A process for producing steroidal alcohols
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0001622A1

  公开（公告）日：1979-05-02

  Steroidal alcohols are produced by cultivating a micro- organisrn belonging to the genus Mycobacterium and capable of producing 20 α-hydroxymethylpregna-1,4- dien-3- one or 20α-hydroxymethylpregn-4- en-3-one as a main product in the presence of a sterol substrste.

  类固醇醇是通过培养一种属于分枝杆菌属的微生物而产生的，这种微生物能够在固醇底物存在的情况下产生 20α-hydroxymethylpregna-1,4- dien-3- one 或 20α-hydroxymethylpregn-4- en-3-one 作为主要产物。
• Microorganisms and their use in producing androst-4-ene-3,17-dione
  申请人：THE UPJOHN COMPANY

  公开号：EP0008214A1

  公开（公告）日：1980-02-20

  A novel mutant, Mycobacterium fortuitum CBS 313. 79, can be used in a microbiological process to selectively transform steroids having 17-alkyl side chains of from 2 to 10 carbon atoms, to yield androst-4-ene-3,17-dione (AD) as essentially the sole transformed product. AD is a valuable intermediate in the synthesis of useful steroids. CBS 313.79 can be obtained by mutation of the novel adaptive mutant Mycobacterium fortuitum CBS 314.79.

  一种新型突变体，即福氏分枝杆菌 CBS 313.79，可用于微生物工艺中，选择性地转化具有 2 至 10 个碳原子的 17-烷基侧链的类固醇，以产生雄甾-4-烯-3,17-二酮（AD）作为唯一的转化产物。 AD 是合成有用类固醇的重要中间体。 CBS 313.79 可通过突变新型适应性突变体福氏分枝杆菌 CBS 314.79 而获得。
• PREGNANE DERIVATIVES AND PROCESS FOR THEIR PREPARATION
  申请人：KURARAY CO., LTD.

  公开号：EP0321572A1

  公开（公告）日：1989-06-28

  Pregnane derivatives represented by general formula (I) (wherein A1 represents a hydrogen atom or a hydroxy group, A2 represents a substituent such as a hydroxy group when A1 represents a hydrogen atom, or A2 represents a hydrogen atom when A1 represents a hydroxy group, or A1 and A2 are combined together to form an oxo group; 01 represents a substituent such as a hydroxy group, and D2 represents a hydrogen atom, or D1 and D2 are combined together to form an epoxy group or a single bond; D3, D5 and D7 each represents a hydrogen atom, D4 represents a hydroxy group, and D6 represents a substituent such as a hydroxy group, or D3 and D4 may be combined together to form an epoxy group or a single bond, or D4 and D5 may be combined together to form a single bond, D5 and D6 may be combined together to form an epoxy group or a single bond, or D6 and D7 may be combined together to form a single bond; and X1 and X2 each represents a lower alkoxy group or, when combined together, they represent a lower alkylenedioxy or oxo group) and a process for their preparation. The pregnane derivatives are useful as intermediates for synthesizing vitamin D3 having a hydroxy group in the 1α-position.

  由通式(I)代表的孕烷衍生物（其中A1代表氢原子或羟基，当A1代表氢原子时A2代表羟基等取代基，或当A1代表羟基时A2代表氢原子，或A1和A2结合在一起形成氧代基；01代表羟基等取代基，D2代表氢原子，或D1和D2结合在一起形成环氧基或单键；D3、D5 和 D7 各自代表氢原子，D4 代表羟基，D6 代表取代基，如羟基，或 D3 和 D4 可结合在一起形成环氧基或单键，或 D4 和 D5 可结合在一起形成单键，D5 和 D6 可结合在一起形成环氧基或单键，或 D6 和 D7 可结合在一起形成单键；X1和X2各自代表一个低级烷氧基，或者当它们结合在一起时，代表一个低级烷二氧基或氧化基团）及其制备方法。孕烷衍生物可作为合成 1α 位具有羟基的维生素 D3 的中间体。