2,2,5,7,8-Pentamethyl-6-Chromanol
(Synonyms: 3,4-二氢-2,2,5,7,8-五甲基-2H-1-苯并吡喃-6-酚,PMC) 目录号 : GC35069
2,2,5,7,8-Pentamethyl-6-Chromanol (PMC) 是维生素 E (α-tocopherol) 的抗氧化部分。2,2,5,7,8-Pentamethyl-6-Chromanol 具有有效的雄激素受体 (androgen receptor) 信号调节和抗前列腺癌细胞系的抗癌活性。
Cas No.:950-99-2
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2,2,5,7,8-Pentamethyl-6-Chromanol (PMC) is the anti-oxidant moiety of vitamin E (α-tocopherol). 2,2,5,7,8-Pentamethyl-6-Chromanol has potent androgen receptor (AR) signaling modulation and anti-cancer activity against prostate cancer cell lines[1].
[1]. Kyriakopoulos CE, et al. A multicenter phase 1/2a dose-escalation study of the antioxidant moiety of vitamin E 2,2,5,7,8-pentamethyl-6-chromanol (APC-100) in men with advanced prostate cancer. Invest New Drugs. 2016 Apr;34(2):225-30.
| Cas No. | 950-99-2 | SDF | |
| 别名 | 3,4-二氢-2,2,5,7,8-五甲基-2H-1-苯并吡喃-6-酚,PMC | ||
| Canonical SMILES | OC1=C(C)C(C)=C2C(CCC(C)(C)O2)=C1C | ||
| 分子式 | C14H20O2 | 分子量 | 220.31 |
| 溶解度 | DMSO: 250 mg/mL (1134.76 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.5391 mL | 22.6953 mL | 45.3906 mL |
| 5 mM | 0.9078 mL | 4.5391 mL | 9.0781 mL |
| 10 mM | 0.4539 mL | 2.2695 mL | 4.5391 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Reduction of 8a-hydroxy-2,2,5,7,8-pentamethyl-6-chromanone
Redox Rep 2002;7(5):251-5.PMID:12688504DOI:10.1179/135100002125000730.
Two-electron oxidation of 2,2,5,7,8-Pentamethyl-6-Chromanol (PH), a model compound of alpha-tocopherol, gives the unstable 8a-hydroxy-2,2,5,7,8-pentamethyl-6-chromanone (POH) which rearranges to form stable 2-(3-hydroxy-3-methylbutyl)-3,5,6-trimethyl-1,4-benzoquinone (PQ). POH and PQ are isomers which have the same oxidation state. The aim of this work was to compare the ease of reduction of POH and PQ at room temperature using a variety of biological and chemical reductants in a reductant:POH (PQ) ratio of 20:1 (or 16:1). Ascorbic acid completely reduced POH to PH in 20 min, but had no effect on PQ after 40 min. Sodium ascorbate did not reduce POH or PQ at all after 40 min. Sodium dithionite reduced POH to PH (85%) in 20 min, but reduced PQ to its hydroquinone, PQH2 (67%) in 40 min. Dithiothreitol produced a slight reduction of POH to PH (21%) but reduced PQ to PQH2 (69%). NADH/FAD reduced POH and PQ to PQH2 (73% and 42%, respectively) in 10 min. It was concluded that POH is easier to reduce than PQ and more likely to form PH as a product, particularly under conditions of mild acidity.
Oxidation of the α-tocopherol model compound 2,2,5,7,8-Pentamethyl-6-Chromanol in the presence of alcohols
Lipids 1992 Jun;27(6):447-53.PMID:27519671DOI:10.1007/BF02536387.
Oxidation of the vitamin E model compound, 2,2,5,7,8-Pentamethyl-6-Chromanol (1b) byt-butyl hydroperoxide in chloroform has been studied in the presence of ethanol, heptanol and cholesterol. In the absence of an alcohol, the major products were the spirodimer (13b) and spirotrimer (14b) of 1b, together with 1H,2,3-dihydro-3,3,5,6,9,10,11a(R)-heptamethyl-7a(S)-(3-hydroxy-3-methylbutyl)-pyrano[2,3-a] xanthene 8(7aH), 11(11aH) dione (6b). In the presence of ethanol, heptanol and cholesterol, the major products were 5-ethoxymethyl-2,2,7,8-tetramethyl-6-chromanol (16b), 5-heptoxymethyl-2,2,7,8-tetramethyl-6-chromanol (17) and 5-cholesteroxymethyl-2,2,7,8-tetramethyl-6-chromanol (18). However, when water was present in a homogeneous reaction, the most rapidly formed product was 2-(3-hydroxy-3-methylbutyl)-3,5,6-trimethyl-1,4-benzoquinone (5b). Compounds 13b, 14b, 16b, 17 and 18 are formedvia a quinone methide intermediate, and compound 5b is formedvia a phenoxylium ion. The phenoxylium species appears to be the preferred intermediate when water is present, whereas the quinone methide species is prefered in the absence of water.
A multicenter phase 1/2a dose-escalation study of the antioxidant moiety of vitamin E 2,2,5,7,8-Pentamethyl-6-Chromanol (APC-100) in men with advanced prostate cancer
Invest New Drugs 2016 Apr;34(2):225-30.PMID:26924129DOI:10.1007/s10637-016-0334-y.
Background: A phase 1/2a dose escalation study of APC-100 (2,2,5,7,8-Pentamethyl-6-Chromanol) was conducted to determine maximum tolerated dose (MTD), recommended phase 2 dose, toxicities and efficacy in men with castrate-resistant prostate cancer (CRPC). Methods: This open label phase 1/2a study utilizes a time-to-event reassessment method (TITE-CRM) design. Patients in cohorts of 3 were treated with escalating doses of APC-100 (900 mg-2400 mg) orally once daily continuously. Cycles were 28 days. Results: Twenty patients with CRPC were enrolled in the dose escalation cohort. One possible DLT (elevated ALT) was seen at dose level 1. No other DLTs were seen and no dose reductions were required. Most frequent AEs included nausea (grade 1 in 6 patients) and elevated transaminases (grade 1-3 in 5 patients). After enrolment of 20 patients the MTD was not reached, however the maximal feasible dose was exceeded due to the number of capsules ingested. Five of the 20 patients had stable disease as their best response. The median progression free survival (PFS) for the cohort was 2.8 months (range 1-8). Conclusions: APC-100 is a novel agent with dual mechanism of action functioning both as potent antioxidant as well as antiandrogen. No detectable APC-100 was found in the plasma at dose level 5 (2100 mg) and it was felt that maximal feasibility was nearly reached. APC-100 is being reformulated as a tablet to allow further dose escalation. Once a recommended phase 2 dose is established, future studies in prostate cancer chemoprevention should be conducted.
Co-oxidation of 2,2,5,7,8-Pentamethyl-6-Chromanol and diphenyl disulfide with 3-chloroperoxybenzoic acid
Redox Rep 2001;6(3):191-3.PMID:11523597DOI:10.1179/135100001101536184.
The aim of this study was to determine whether disulfides could serve as protective antioxidants for alpha-tocopherol or vice versa. The chosen reaction system was a co-oxidation of the model compound of alpha-tocopherol, 2,2,5,7,8-Pentamethyl-6-Chromanol (PMC), and diphenyl disulfide (1) by 3-chloroperoxybenzoic acid. The rate of oxidation of the disulfide was approximately twice as fast as that of PMC when each compound was oxidised separately. However, when they were co-oxidised, the rate of loss of PMC increased while that of the disulfide decreased. The reason appeared to be that the disulfide was preferentially oxidised to the thiosulfinate (2) and the thiosulfonate (3) which then reacted with unchanged PMC to form compound (4), the major product, and benzenethiol. Benzenethiol was then re-oxidised to the disulfide.
Reaction of 2,2,5,7,8-Pentamethyl-6-Chromanol, an alpha-tocopherol analogue, with NO in the presence of oxygen
Bioorg Med Chem Lett 2000 Dec 18;10(24):2709-12.PMID:11133074DOI:10.1016/s0960-894x(00)00563-1.
An alpha-tocopherol model compound, 2,2,5,7,8-Pentamethyl-6-Chromanol, reacted with nitric oxide (NO) in the presence of various amounts of oxygen to afford four major products. Distribution of the products was varied depending on the ratio of NO and O2, and the preincubation time of NO and O2.