17Α-羟基-16Β-甲基孕烯醇 | 13900-61-3

• 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: 17Α-羟基-16Β-甲基孕烯醇
• 中文别名: 17Alpha-羟基-16Β-甲基孕烯醇；17α-羟基-16β-甲基孕烯醇
• 英文名称: 3β.17α-Dihydroxy-16α-methyl-pregnen-(5)-on-(20)
• 英文别名: 3β,17α-Dihydroxy-16β-methyl-5-pregnen-20-on；16β-Methyl-5-pregnene-3β,17α-diol-20-one；3-beta,17-alpha-Dihydroxy-16-beta-methylpregn-5-en-20-one；1-[(3S,8R,9S,10R,13S,14S,16S,17R)-3,17-dihydroxy-10,13,16-trimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 13900-61-3
• 化学式: C₂₂H₃₄O₃
• 分子量: 346.51
• InChiKey: MDCCMZGGNCMFPQ-RGEWOSBMSA-N

物化性质

• 熔点：
  224-230 °C
• 沸点：
  483.9±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)
• 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)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25

SDS

Name:	17-alpha-Hydroxy-16 beta-methylpregnenolone Material Safety Data Sheet
Synonym:	3 beta, 17-alpha-Dihydroxy-16 beta-methyl-5-pregnen-20-on
CAS:	13900-61-3

Section 1 - Chemical Product MSDS Name:17-alpha-Hydroxy-16 beta-methylpregnenolone Material Safety Data Sheet
Synonym:3 beta, 17-alpha-Dihydroxy-16 beta-methyl-5-pregnen-20-on

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13900-61-3	17-alpha-Hydroxy-16 beta-methylpregnen	100	237-673-7

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

---

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 irritation of the digestive tract. 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.

---

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.
Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
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 immediately.
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.
Notes to Physician:

---

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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

---

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. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Hormones and antibiotics room.

---

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 adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 13900-61-3: 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:
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 227.00 - 229.00 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: C22H34O3
Molecular Weight: 346.51

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13900-61-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
17-alpha-Hydroxy-16 beta-methylpregnenolone - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 13900-61-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13900-61-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13900-61-3 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  17Α-羟基-16Β-甲基孕烯醇 在 溴 、 lithium carbonate 、 对甲苯磺酸 、 三氟乙酸酐 、 lithium bromide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 17α-acetoxy-16β-methylpregna-4,6-diene-3,20-dione
  参考文献：
  名称：

  Androgenic and anti-androgenic effects of progesterone derivatives with different halogens as substituents at the C-6 position

  摘要：

  The pharmacological activities of four pregnane derivatives: 17 alpha-hydroxy-16 beta-methylpregna-4,6-diene-3,20-dione (7), 17 alpha-acetoxy-16 beta-methylpregna-4,6-diene-3,20-dione (8), 17 alpha-acetoxy-6-bromo-16 beta-methylpregna-4,6-diene-3,20-dione (10), and 17 alpha-acetoxy-6-chloro-16 beta-methylpregna-4,6-diene-3,20-dione (11), were determined. The derivatives were evaluated on gonadectomized male hamster flank organs and seminal vesicles. The results indicate that topical applications of testosterone (T) on the flank organs increased the diameter of the pigmented spot. Similarly, the same phenomenon occurred on the glands treated with compound 11, whereas compound 10 decreased the size of the spot significantly. In this study, we determined the effects of several new steroids on the conversion of T to DHT in flank organs and seminal vesicles. The results show that compound 10 inhibited T conversion to DHT, but compound 11, at a dose of 200 mu g, stimulated T conversion in both flank organs and seminal vesicles. However, when 2 mg of compound 11 was applied, it inhibited the conversion of T to DHT, suggesting that this compound also represses gonadotropin release. The difference between compounds 10 and II involves the electronegativity of the halogen at the C-6 position of the progesterone skeleton. These data clearly indicate that by decreasing the electronegativity of the halogen at C-6 (compound 10), 5 alpha-reductase is inhibited in both tissues and at different pHs. On the other hand, when the electronegativity of the halogen atom was increased (11), there was a much lower inhibitory effect on the conversion of T to DHT. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00018-5
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 吡啶 、 sodium hydroxide 、 copper(l) iodide 、 双氧水 、 氢气 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 103.0h， 生成 17Α-羟基-16Β-甲基孕烯醇
  参考文献：
  名称：

  Evaluation of New Pregnane Derivatives as 5.ALPHA.-Reductase Inhibitor.

  摘要：

  本研究的目的是合成几种新的孕烷衍生物，并将它们作为抗雄激素进行评估。从市售的 16-脱氢孕烯醇酮醋酸酯（7）中，合成了两种新的类固醇化合物：17α-hydroxy-17β-methyl-16β-phenyl-D-homoandrosta-1, 4.6-triene-3, 20-dione (18) 和 17α-acetoxy-17β-methyl-16β-phenyl-D-homoandrosta-1, 4.6-triene-3, 20-dione (19)。新化合物 18 和 19 以及之前合成的中间体 7、8、13、16 和 17 的 5α 还原酶抑制作用在三种不同的模型中进行了测定：性腺切除的仓鼠侧腹器官直径大小、侧腹器官脂质中[1, 2-14C]sodium acetate 的结合以及甲壳青霉将[3H]睾酮（T）转化为[3H]双氢睾酮（DHT）。对这些类固醇的评估是在三个不同对照组的基础上进行的：一组用药物治疗，第二组用睾酮治疗，第三组用睾酮加非那雄胺治疗。这项工作的药理结果表明，T 能显著增加仓鼠腹侧器官上色素斑的直径（p<0.05），并能显著增加性腺切除仓鼠腹侧器官中脂质中标记的醋酸钠的掺入量（每个腺体从 0.125 到 0.255 nmol）。在这项研究中，我们还观察到甲壳青霉肉汤将[3H]T转化为[3H]DHT的方式与侧腹器官的转化方式类似。所有实验都表明，非那雄胺以及类固醇 7、8、13、16-19 能显著减少甲壳青霉中 T 向 DHT 的转化。这些化合物还能减小侧腹器官中色素斑的大小，并减少放射性标记的醋酸钠在脂质中的结合；T 和对照样本（仅用载体处理）被用来进行比较。显然，4,6-二烯-3,20-二酮分子和 C-17 酯基的存在对所用参数产生了更大的抑制作用。该研究的数据还表明，用于药理评估的三种模型表现出的结果具有可比性。

  DOI：

  10.1248/cpb.49.525

文献信息

• Molecular Interactions of New Pregnenedione Derivatives
  作者：Eugene Bratoeff、Elena Ramírez、Eugenio Flores、Norma Valencia、Mauricio Sánchez、Ivonne Heuze、Marisa Cabeza

  DOI：10.1248/cpb.51.1132

  日期：——

  The in vitro inhibitory activity of five new progesterone derivatives: 17α-hydroxy-16β-methylpregna-1,4,6-triene-3,20-dione 1; 16β-methyl-17α-toluoyloxypregna-1,4,6-triene-3,20-dione 2; 17α-hydroxy-6-methylenepregn-4-ene-3,20-dione 3; 6-methylene-17α-toluoyloxypregn-4ene-3,20-dione 4 and 17α-(p-bromobenzoyloxy)-6-methylenepregn-4-ene-3,20-dione 5 was determined. These compounds were evaluated as 5α-reductase inhibitors as well as antagonists for the androgen receptor. Compounds 1, 2, 3, 4 and 5 showed the following inhibitory activity for the 5α-reductase enzyme with IC50 values of: 1 (1.65 μM), 2 (10 μM), 3 (19 nM), 4 (100 nM) and 5 (100 nM). The results of this study also showed the effect of increasing concentrations of the novel steroids upon [3H]dihydrotestosterone binding to androgen receptors from male hamster prostate. The Ki values for compounds 1, 2, 3, 4, 5 and dihydrotestosterone showed the following order of affinity for the androgen receptor: 4>5>dihydrotestosterone>2>3>1. The overall data indicated that all synthesized compounds 1, 2, 3, 4 and 5 are inhibitors of the 5α-reductase enzyme present in the hamster prostate. In addition compounds 1, 2, 3, 4 and 5 also presented an affinity for the androgen receptor.

  五种新的孕酮衍生物体外抑制活性研究：17α-羟基-16β-甲基孕甾-1,4,6-三烯-3,20-二酮1；16β-甲基-17α-甲苯甲酰氧基孕甾-1,4,6-三烯-3,20-二酮2；17α-羟基-6-亚甲基孕甾-4-烯-3,20-二酮3；6-亚甲基-17α-甲苯甲酰氧基孕甾-4-烯-3,20-二酮4 和 17α-(对溴苯甲酰氧基)-6-亚甲基孕甾-4-烯-3,20-二酮5 的体外抑制活性被测定。这些化合物被评估为 5α-还原酶抑制剂以及雄激素受体的拮抗剂。化合物 1、2、3、4 和 5 显示出对 5α-还原酶的以下抑制活性，IC50 值分别为：1 (1.65 μM)，2 (10 μM)，3 (19 nM)，4 (100 nM) 和 5 (100 nM)。本研究的结果还显示了新型类固醇浓度增加对 [3H] 二氢睾酮与雄性仓鼠前列腺雄激素受体结合的影响。对于雄激素受体，化合物 1、2、3、4、5 和二氢睾酮的 Ki 值显示出以下亲和力顺序：4>5>二氢睾酮>2>3>1。总体数据表明，所有合成的化合物 1、2、3、4 和 5 都是仓鼠前列腺中存在的 5α-还原酶的抑制剂。此外，化合物 1、2、3、4 和 5 也显示出对雄激素受体的亲和力。
• Synthesis and Pharmacological Evaluation of New 16-Methyl Pregnane Derivatives.
  作者：Elena Ramirez、Marisa Cabeza、Ivonne Heuze、Edgar Gutiérrez、Eugene Bratoeff、Marisol Membrillo、Alfonso Lira

  DOI：10.1248/cpb.50.15

  日期：——

  pharmacological activity of several new pregnane derivatives 15-19 were determined on gonadectomized male hamster flank organs, seminal vesicles and in vitro conversion of testosterone (T) to dihydrotestosterone (DHT) as 5alpha-reductase inhibitors. Steroids 15-19 decreased the diameter of the pigmented spot in the flank organs as compared to the T treated animals; in this model, steroids 16 and 19 showed a higher

  确定了几种新的孕烷衍生物15-19的药理活性，将其脱去腺的雄性仓鼠胁腹器官，精囊和体外睾丸激素（T）转化为5α-还原酶抑制剂的二氢睾丸激素（DHT）。与经T处理的动物相比，类固醇15-19减少了胁腹器官色素斑的直径；在该模型中，类固醇16和19的活性高于市售非那雄胺3。注射T会增加精囊的重量。当与T一起注射时，化合物15-19降低了精囊的重量，因此显示出抗雄激素作用。三烯酮19显示出比非那雄胺明显更高的活性。类固醇15-19抑制了性腺切除的雄性仓鼠精囊匀浆中[3H] T到[3H] DHT的体外代谢。化合物18和19显示出比非那雄胺更高的抗雄激素作用。正如我们小组先前观察到的那样，这种生物活性的增强可能归因于甾体骨架的共面性。环氧化合物16的高抗雄激素活性可能是由于奥昔兰环与5α-还原酶的亲核部分开环导致的结果，因此导致稳定的加合物，同时伴随该酶的失活。正如我们小组先前观察到的那样，这种生物
• Antiandrogenic Effect of 16-Substituted, Non-substituted and D-Homopregnane Derivatives.
  作者：Eugene A. BRATOEFF、H. HERRERA、E. RAMIRES、K. SOLORZANO、E. MURILLO、A. QUIROZ、M. CABEZA

  DOI：10.1248/cpb.48.1249

  日期：——

  The pharmacological activities of 12 pregnane derivatives (4-15) were determined on gonadectomized male hamster flank organs and seminal vesicles as antiandrogens and as 5α-reductase inhibitors. The results from this study indicate that subcutaneous injection of testosterone for 3 d increased the diameter of the pigmented spot in the flank organs, whereas finasteride when injected with testosterone decreased the size of the spot significantly when steroids 4-15 were injected together with testosterone, the diameter of the flank organs of gonadectomized male hamsters, decreased significantly (p<0.005) compared to testosterone. Compound 11 was the most active steroid and reduced the diameter of the pigmented spot more than the other synthesized steroids or finasteride. Subcutaneous injections of testosterone to gonadectomized animals restore the seminal vesicle size lost upon castration. Injection of testosterone plus finasteride decreased significantly the weight of these glands (p<0.005). Steroids 5-15 when injected with testosterone decreased the weight of the seminal vesicles compared to testosterone. Finasteride is a good inhibitor of the conversion of testosterone to dihydrotestosterone (DHT) (low formation of DHT) measured as pmole of DHT/g of protein/h. Steroids 6-15 inhibited the conversion of testosterone to DHT as compared to testosterone however finasteride and 10 appeared to be the most effective compounds. Castration increases the protein content of the seminal vesicles (control) expressed as μg/mg of tissues. Testosterone tends to decrease it significantly, as did compounds 4, 5, 7, 9, and 15. We demonstrated that DHT as well as cyproterone acetate and steroids 5, 6, 8, 9, 11, and 14 at increasing non radioactive steroid concentration, inhibited the binding of [3H]DHT to cytosolic androgen receptor (AR), as indicated by its K1 values. However, 4, 7, 10, 12, and 13 did not have any inhibitory effect.

  本研究测定了12种孕烷衍生物（4-15）作为抗雄激素和5α还原酶抑制剂在性腺切除的雄性仓鼠侧腹器官和精囊上的药理活性。研究结果表明，皮下注射睾酮 3 d 后，仓鼠侧腹器官色素斑的直径增大，而与睾酮同时注射非那雄胺后，色素斑的大小明显缩小。化合物 11 是活性最强的类固醇，它比其他合成类固醇或非那雄胺更能减少色斑的直径。对性腺切除的动物皮下注射睾酮可恢复阉割后丧失的精囊大小。注射睾酮和非那雄胺可显著减少这些腺体的重量（p<0.005）。与睾酮相比，与睾酮一起注射的类固醇5-15会减少精囊的重量。非那雄胺能很好地抑制睾酮向双氢睾酮（DHT）的转化（DHT的形成较低），以DHT/克蛋白质/小时的pmole来衡量。与睾酮相比，类固醇 6-15 可抑制睾酮向 DHT 的转化，但非那雄胺和 10 似乎是最有效的化合物。阉割会增加精囊（对照组）的蛋白质含量，单位为微克/毫克组织。睾酮和化合物 4、5、7、9 和 15 都会显著降低精囊蛋白含量。我们的研究表明，DHT、醋酸环丙孕酮和类固醇 5、6、8、9、11 和 14 在非放射性类固醇浓度增加的情况下，会抑制 [3H]DHT 与细胞膜雄激素受体（AR）的结合，如其 K1 值所示。然而，4、7、10、12 和 13 没有任何抑制作用。
• Method of forming subtraction images
  申请人：Arakawa Satoshi

  公开号：US20050195943A1

  公开（公告）日：2005-09-08

  A radiation image signal is acquired from a radiation image of an object before being injected with a contrast medium, and a radiation image signal is acquired from a radiation image of the same object after being injected with the contrast medium. A subtraction process for subtracting image signal components of a plurality of the thus acquired radiation image signals, which image signal components represent corresponding pixels in the radiation images represented by the plurality of the radiation image signals, from one another is performed. A contrasted radiation image, in which a pattern of a specific structure of the object having been contrasted with the contrast medium in the radiation image has been extracted or enhanced, is thus formed. The contrast medium is a liposome, which contains a hydrophobic iodine compound as a film forming constituent.

  在注入造影剂之前，从物体的辐射图像中获取辐射图像信号，在注入造影剂之后，从同一物体的辐射图像中获取辐射图像信号。执行一个减法过程，将由此获取的多个辐射图像信号的图像信号分量相互减去，这些图像信号分量代表多个辐射图像信号所代表的辐射图像中的相应像素。这样就形成了对比辐射图像，其中提取或增强了辐射图像中被对比介质对比的物体的特定结构的图案。对比介质是一种脂质体，它含有一种疏水性碘化合物作为成膜成分。
• 16-Alkylated Progesterones
  作者：Elliot. Shapiro、Theodore. Legatt、Lois. Weber、Merl. Steinberg、A. Watnick、M. Eisler、Marilyn Gilmore. Hennessey、C. T. Coniglio、W. Charney、Eugene P. Oliveto

  DOI：10.1021/jm01240a010

  日期：1962.9