6,13-Bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol | 38966-21-1

• 物质功能分类: 原料药 - 抗生素类药物 - 其它抗生素类药
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6,13-Bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol
• CAS: 38966-21-1
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.5
• InChiKey: NOFOAYPPHIUXJR-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220°C
• 比旋光度：
  D27 +12° (c = 1 in methanol)
• 沸点：
  394.61°C (rough estimate)
• 密度：
  1.0057 (rough estimate)
• 闪点：
  87℃
• 溶解度：
  乙醇：可溶1mg/mL（在4°C下至少稳定一周。）
• 稳定性/保质期：

   

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S24
• WGK Germany：
  1,3
• 海关编码：
  29419090
• 储存条件：
  本品应密封并在4℃干燥条件下保存。

SDS

Name:	(+)-Aphidicolin Material Safety Data Sheet
Synonym:	8,11a-Methano-11aH-cyclohepta(a)naphthalene-4,9-dimethanol; tetradecahydro-3,9-dihydroxy 4,11b-dimethyl-,(3R-(3-alpha,4-alpha, 4a-alpha, 6a-beta, 8-beta, 9-beta, 11a-beta, 11beta))-
CAS:	38966-21-1

Section 1 - Chemical Product MSDS Name:(+)-Aphidicolin Material Safety Data Sheet
Synonym:8,11a-Methano-11aH-cyclohepta(a)naphthalene-4,9-dimethanol; tetradecahydro-3,9-dihydroxy 4,11b-dimethyl-,(3R-(3-alpha,4-alpha, 4a-alpha, 6a-beta, 8-beta, 9-beta, 11a-beta, 11beta))-

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
38966-21-1	(+)-Aphidicolin	100.0	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.
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.

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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:
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:
Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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:

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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. 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.

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

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. 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. Keep refrigerated. (Store below 4C/39F.)

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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 adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 38966-21-1: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: off-white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C28H26N4O3
Molecular Weight: 466.5

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, electrical sparks.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 38966-21-1: PB9185000 LD50/LC50:
Not available.
Carcinogenicity:
(+)-Aphidicolin - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Products which are considered hazardous for supply are classified as Special Waste and the disposal of such chemicals is covered by regulations which may vary according to location. Contact a specialist disposal company or the local waste regulator for advice. Empty containers must be decontaminated before returning for recycling.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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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# 38966-21-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 38966-21-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 38966-21-1 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

生物活性方面，aphidicolin 是一种 DNA 聚合酶 α 和 δ 的抑制剂，通过干扰 DNA 聚合酶的活性来阻止有丝分裂细胞的分裂。它是由 Cephalosporium aphidicola 产生的抗生素，并且是细胞脱氧核糖核酸合成的有效抑制剂，能够强烈抑制单纯疱疹病毒的生长。此外，在人早幼粒细胞白血病细胞系中，aphidicolin 还可以通过诱导阿拉伯糖基核苷引起细胞凋亡（apoptosis）。

反应信息

• 作为反应物：
  描述：

  N-苄氧羰基甘氨酸 、 6,13-Bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol 生成
  参考文献：
  名称：

  Aphidicolane derivatives, their preparation and pharmaceutical compositions comprising them

  摘要：

  公式为Aphidicolane衍生物：其中R1代表氢或羟基基团，R2代表羟基或甲基基团，或CR1R2基团代表酮基团；R3代表甲酰基或羟甲基基团，或代表-CH20.CO.OR6基团，其中R6代表定义的基团，或R2和R3连接在一起形成-O.CO.OCH2-基团；R4代表羟基基团；R5代表甲酰基基团、羟基烷基基团-(CH2)1-3OH、基团-CHR7OH，其中R7代表定义的基团，或R5代表偶氮甲基或吡咯啉羰基氧甲基基团，或代表-CH20.CO.OR8基团，其中R8代表定义的基团，或R5代表基团-CH2O.CO.(CH2)m.CR11R12.(CH2)n.NR9R10.，其中m，n，R9，R10，R11和R12具有定义的值，或R5代表基团-CH2O.SO2.R13，其中R13代表定义的基团；或R4和R5连接在一起形成-O.CH2-或-O.CO.OCH2-基团；并且在适当情况下，它们的药物可接受的盐。制备该类Aphidicolane衍生物的过程。包括该化合物和药物稀释剂或载体的制药组合物。该化合物具有抑制DNA含量病毒的活性，并抑制某些肿瘤的生长。

  公开号：

  EP0112603A1
• 作为产物：
  描述：

  methyl (1R,2S,5R,10R,11R,14S,16R,17S,19R)-2,7,7,10-tetramethyl-6,8,18-trioxahexacyclo[14.4.1.01,14.02,11.05,10.017,19]henicosane-17-carboxylate 以100的产率得到6,13-Bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol
  参考文献：
  名称：

  Tetrahedron Letters 1988, 29, 2793-2796

  摘要：

  DOI：

文献信息

• Tetrahedron Letters 1988, 29, 2793-2796
  作者：

  DOI：——

  日期：——
• Aphidicolane derivatives, their preparation and pharmaceutical compositions comprising them
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0112603A1

  公开（公告）日：1984-07-04

  Aphidicolane derivatives of the formula: wherein R1 stands for hydrogen or a hydroxy radical, R2 stands for a hydroxy or methyl radical, or the group CR1 R2 stands for a keto group; R3 stands for a formyl or hydroxymethyl radical, or for the group -CH20.CO.OR6, wherein R6 stands for a defined radical or R2 and R3 are joined together to form the group -O.CO.OCH2-; R4 stands for a hydroxy radical; R5 stands for a formyl radical, a hydroxyalkyl radical -(CH2)1-3OH, a radical -CHR7OH, wherein R7 stands for a defined radical, or R5 stands for an azidomethyl or pyrrolidinylcarbonyloxymethyl radical, or for the group -CH20.CO.OR8, wherein R8 stands for a defined radical, or R5 stands for the group -CH2O.CO.(CH2)m.CR11R12.(CH2)n.NR9R10. wherein m, n, R9, R10, R11 and R12 have defined values, or R5 stands for the group -CH2O.SO2.R13, wherein R13 stands for a defined radical; or R4 and R5 are joined together to form the group -O.CH2- or -O.CO.OCH2-; and, where appropriate, pharmaceutically acceptable salts thereof. Processes for the preparation of said aphidicolane derivatives. Pharmaceutical compositions comprising one of thecompounds and a pharmaceutical diluent or carrier. The compounds exhibit inhibitory activity against DNA-containing viruses and they inhibit the growth of some tumours.

  公式为Aphidicolane衍生物：其中R1代表氢或羟基基团，R2代表羟基或甲基基团，或CR1R2基团代表酮基团；R3代表甲酰基或羟甲基基团，或代表-CH20.CO.OR6基团，其中R6代表定义的基团，或R2和R3连接在一起形成-O.CO.OCH2-基团；R4代表羟基基团；R5代表甲酰基基团、羟基烷基基团-(CH2)1-3OH、基团-CHR7OH，其中R7代表定义的基团，或R5代表偶氮甲基或吡咯啉羰基氧甲基基团，或代表-CH20.CO.OR8基团，其中R8代表定义的基团，或R5代表基团-CH2O.CO.(CH2)m.CR11R12.(CH2)n.NR9R10.，其中m，n，R9，R10，R11和R12具有定义的值，或R5代表基团-CH2O.SO2.R13，其中R13代表定义的基团；或R4和R5连接在一起形成-O.CH2-或-O.CO.OCH2-基团；并且在适当情况下，它们的药物可接受的盐。制备该类Aphidicolane衍生物的过程。包括该化合物和药物稀释剂或载体的制药组合物。该化合物具有抑制DNA含量病毒的活性，并抑制某些肿瘤的生长。