16561-29-8

• 常用中文名：12-O-十四烷酰佛波醋酸酯-13
• 常用英文名：12-O-tetradecanoylphorbol-13-acetate
• CAS号：16561-29-8
• 分子式：C₃₆H₅₆O₈
• 分子量：616.825
• 相关类别： 化学试剂 有机试剂 酯类 酸酯类化合物
• 发布时间：2018-12-06 03:09:12
• 更新时间：2024-01-08 10:22:34
• Phorbol 12-myristate 13-acetate (PMA) 是一种佛波酯,是常用的 PKC 活化剂。

名称

• 中文名: 佛波醇12-十四酸酯13-乙酸酯
• 英文名: phorbol 13-acetate 12-myristate
• 中文别名: 12-豆蔻酸-13-乙酸佛波醇
• 英文别名: 4β-Phorbol 12-myristate 13-acetate; Tetradecanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester; TPA; PMA; 12-O-Tetradecanoylphorbol-13-acetate; tetradecanoylphorbol acetate; MFCD00036736; phorbol 13-acetate 12-myristate; (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-Acetoxy-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate; 12-O-Tetradecanoylphorbol 13-acetate; 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate; (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl tetradecanoate; Phorbol 12-myristate 13-acetate

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 698.1±55.0 °C at 760 mmHg
• 分子式: C₃₆H₅₆O₈
• 分子量: 616.825
• 闪点: 208.1±25.0 °C
• 精确质量: 616.397522
• PSA: 130.36000
• LogP: 7.71
• 外观性状: 白色至灰白色固体
• 蒸汽压: 0.0±5.0 mmHg at 25°C
• 折射率: 1.553
• 储存条件: 库房通风低温干燥,与食品分开储运
• 水溶解性: DMSO: DMSO solutions can be stored dark at −20?#x00b0;C for at least six months.soluble
• 分子结构:

  1、 摩尔折射率：168.29

  2、 摩尔体积（m³/mol）：525.6

  3、 等张比容（90.2K）：1404.3

  4、 表面张力（dyne/cm）：50.9

  5、 极化率（10^-24cm³）：66.71

• 计算化学:

  1.疏水参数计算参考值（XlogP）:6.5

  2.氢键供体数量:3

  3.氢键受体数量:8

  4.可旋转化学键数量:17

  5.互变异构体数量:3

  6.拓扑分子极性表面积130

  7.重原子数量:44

  8.表面电荷:0

  9.复杂度:1150

  10.同位素原子数量:0

  11.确定原子立构中心数量:8

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1.性状：未确定

  2.密度（g/mL,25/4℃）：未确定

  3.相对蒸汽密度（g/mL,空气=1）：未确定

  4.熔点（ºC）：未确定

  5.沸点（ºC,常压）：未确定

  6.沸点（ºC,5.2kPa）：未确定

  7.折射率：未确定

  8.闪点（ºC）：未确定

  9.比旋光度（º）：未确定

  10.自燃点或引燃温度（ºC）：未确定

  11.蒸气压（kPa,25ºC）：未确定

  12.饱和蒸气压（kPa,60ºC）：未确定

  13.燃烧热（KJ/mol）：未确定

  14.临界温度（ºC）：未确定

  15.临界压力（KPa）：未确定

  16.油水（辛醇/水）分配系数的对数值：未确定

  17.爆炸上限（%,V/V）：未确定

  18.爆炸下限（%,V/V）：未确定

  19.溶解性：DMSO: DMSO solutions can be stored dark at −20?#x00b0;C for at least six months.soluble

生物活性

• 描述: Phorbol 12-myristate 13-acetate (PMA) 是一种佛波酯,是常用的 PKC 活化剂。
• 相关类别:
  信号通路 >> 表观遗传学 >> PKC
  信号通路 >> TGF-beta/Smad 信号通路 >> PKC
  研究领域 >> 炎症/免疫
  天然产物 >> 其他
• 靶点:

  PKC:11.7 nM (EC50)

• 体外研究: 为了检查PKC在p38MAPK磷酸化中的作用,用PKC活化剂PMA(100nM)刺激细胞,其模拟PKC的天然活化剂DAG与PKC的C1区的结合。在与αT3-1细胞中GnRH观察到的类似的两种细胞类型中观察到PMA的p38MAPK磷酸化,即缓慢的持续激活(分别在30分钟时为3.2倍和3.6倍)。由GnRH和PMA激活的PKC在p38MAPK磷酸化中起不同作用的矛盾发现可以通过PKC的差异定位来解释。 αT3-1细胞中p38MAPK磷酸化的基础,GnRH-和PMA-刺激是通过电压门控Ca2 +通道和Ca2 +动员的Ca2 +流入介导的,而在分化的LβT2促性腺细胞中,它仅通过Ca2 +动员介导[2]。
• 体内研究: PMA是PKC激动剂,其逆转由5-羟基癸酸(5-HD)诱导的损伤。因此,mitoKATP的激活通过PKC途径保护SOD和MDA中的线粒体功能[3]。
• 细胞实验: αT3-1和LβT-2细胞在补充有10％胎牛血清（FCS）和L-谷氨酰胺2mM，青霉素和链霉素（100单位/ mL）的DMEM中在37℃加湿培养箱中培养5％CO2培养。 C。在同一培养基中血清饥饿为0.1％FCS，持续16小时。然后如所示，将GnRH和PMA添加一段时间。通常，αT3-1细胞通过ExGen 500或jetPRIME瞬时转染，而LβT2细胞仅通过jetPRIME转染试剂转染。对于显性阴性（DN）PKC的实验，用1.5μgp38α-GFP和3μg对照载体，pCDNA3或3μgDN-PKC构建体转染αT3-1细胞（在6cm平板中）。对于LβT2细胞，用4μgp38α-GFP以及9μg对照载体，pCDNA3或9μgDN-PKC构建体进行转染（在10cm平板中）。转染后约30小时，将细胞血清饥饿（0.1％FCS）16小时，然后用GnRH或PMA刺激，用冰冷的PBS洗涤两次，用裂解缓冲液处理，然后进行一次冻融循环。收获细胞;离心（15,000×g，15分钟，4℃）后，取上清液进行免疫沉淀实验[2]。
• 动物实验: 大鼠[3]所有实验均用雄性Wistar大鼠（体重250-280g）进行。将125只Wistar大鼠随机分成7组。 （1）假手术组（n = 21）给予侧脑室注射0.9％生理盐水; （2）IR组大鼠（n = 21）在大脑中动脉闭塞（MCAO）前30 min给予侧脑室注射0.9％生理盐水; （3）在MCAO前30分钟，给予Carbenoxolone（CBX）组（n = 21）大鼠侧脑室注射CBX（5μg/ mL×10μL）; （4）在MCAO之前30分钟，给二氮嗪（DZX）组（n = 21）的大鼠腹侧注射DZX（2mM×30μL）; （5）对5-HD组（n = 21）的大鼠进行5-HD（100mM×10μL）的侧脑室注射，10分钟后，在MCAO前15分钟注射DZX; （6）给DZX + Ro组大鼠（n = 15）注射DZX侧脑室，10分钟后，在MCAO前15分钟注射Ro-31-8425（400μg/ kg）; （7）注射5-HD和DZX后，给5-HD + PMA组（n = 15）的大鼠腹膜内注射PMA（200μg/ kg）。
• 参考文献:

  [1]. Xu F, et al. Protein kinase C-mediated Ca2+ entry in HEK 293 cells transiently expressing human TRPV4. Br J Pharmacol. 2003 Sep;140(2):413-21.

  [2]. Mugami S, et al. Differential roles of PKC isoforms (PKCs) and Ca2+ in GnRH and phorbol 12-myristate 13-acetate (PMA) stimulation of p38MAPK phosphorylation in immortalized gonadotrope cells. Mol Cell Endocrinol. 2017 Jan 5;439:141-154.

  [3]. Hou S, et al. Mechanism of Mitochondrial Connexin43's Protection of the Neurovascular Unit under Acute Cerebral Ischemia-Reperfusion Injury. Int J Mol Sci. 2016 May 5;17(5). pii: E679.

  [4]. Zhang T, et al. MPTP-Induced Dopamine Depletion in Basolateral Amygdala via Decrease of D2R Activation Suppresses GABAA Receptors Expression and LTD Induction Leading to Anxiety-Like Behaviors. Front Mol Neurosci. 2017 Aug 7;10:247.

MSDS

Name: Phorbol 12-myristate 13-acetate 99% Material Safety Data Sheet Synonym: PMA; TPA; 12-O-Tetradecanoylphorbol 13-acetat CAS: 16561-29-8 Section 1 - Chemical Product MSDS Name:Phorbol 12-myristate 13-acetate 99% Material Safety Data Sheet Synonym:PMA; TPA; 12-O-Tetradecanoylphorbol 13-acetat Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 16561-29-8 Phorbol 12-myristate 13-acetate 99% unlisted Hazard Symbols: T Risk Phrases: 23/24/25 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Toxic by inhalation, in contact with skin and if swallowed.Cancer suspect agent. Potential Health Effects Eye: May cause eye irritation. Skin: Toxic in contact with skin. Ingestion: Poison by ingestion. Inhalation: Toxic if inhaled. Chronic: Not available. Section 4 - FIRST AID MEASURES Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. Skin: Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Ingestion: Get medical aid immediately. Wash mouth out with 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: 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 water spray, dry chemical, carbon dioxide, or chemical foam. 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. Section 7 - HANDLING and STORAGE Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood. Storage: Store in a cool, dry place. Store in a tightly closed container. Deep freeze (below -20C). Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 16561-29-8: Personal Protective Equipment Eyes: Not available. 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. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Solid Color: colorless to white Odor: Not available. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: Not available. Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: Not available. Specific Gravity/Density: Molecular Formula: C36H56O8 Molecular Weight: 616.3872 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Not available. Conditions to Avoid: Incompatible materials, light, excess heat. Incompatibilities with Other Materials: Strong oxidizing agents, strong bases. Hazardous Decomposition Products: Carbon monoxide, carbon dioxide. Hazardous Polymerization: Will not occur. Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 16561-29-8: QH4377000 LD50/LC50: Not available. Carcinogenicity: Phorbol 12-myristate 13-acetate - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. 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 No information available. IMO No information available. RID/ADR No information available. Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: T Risk Phrases: R 23/24/25 Toxic by inhalation, in contact with skin and if swallowed. Safety Phrases: S 28A After contact with skin, wash immediately with plenty of water. S 36/37/39 Wear suitable protective clothing, gloves and eye/face protection. S 38 In case of insufficient ventilation, wear suitable respiratory equipment. 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# 16561-29-8: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 16561-29-8 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 16561-29-8 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A

安全

• 个人防护装备: dust mask type N95 (US);Eyeshields;Gloves
• 危害码 (欧洲): Xi: Irritant;
• 风险声明 (欧洲): R38
• 安全声明 (欧洲): S36/37
• 危险品运输编码: 2928
• WGK德国: 3
• RTECS号: QH4377000
• 包装等级: II
• 危险类别: 6.1(a)

合成路线

17673-25-5 ~% 16561-29-8

文献：Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, , vol. 23, p. 538 - 546

20839-03-6 ~% 16561-29-8

文献：Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, , vol. 23, p. 538 - 546

20839-03-6 108-24-7 ~% 16561-29-8

文献：Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, , vol. 23, p. 538 - 546

20839-24-1 108-24-7 ~% 16561-29-8

文献：Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, , vol. 23, p. 538 - 546

41621-85-6 112-64-1 ~% 16561-29-8

文献：Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, , vol. 23, p. 538 - 546

上下游产品

上游产品  5
17673-25-5 20839-03-6 108-24-7 41621-85-6
112-64-1
下游产品  0