7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde

• ChemBase编号: 72946
• 分子式: C30H30O8
• 平均质量: 518.5544
• 单一同位素质量: 518.19406792
• SMILES: c1(c(c(c(c2c1c(c(c(c2)C)c1c(c2c(cc1C)c(c(c(c2C=O)O)O)C(C)C)O)O)C(C)C)O)O)C=O
• Canonical SMILES: O=Cc1c(O)c(O)c(c2c1c(O)c(c(c2)C)c1c(C)cc2c(c1O)c(C=O)c(c(c2C(C)C)O)O)C(C)C
• InChI: InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
• InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde
• IUPAC传统名: gossypol
• 别名: Gossypol; (±)-2,2′-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene); (±)-Gossypol from cotton seeds

登记号

• CAS号: 303-45-7
• MDL号: MFCD00017352
• PubChem SID: 162037866; 24895349
• PubChem CID: 3503
• CHEMBL: 51483
• Chemspider ID: 3383
• KEGG ID: C07667
• 美国药典/FDA物质标识码: KAV15B369O
• 维基百科标题: Gossypol

理论计算性质

• Acid pKa: 7.799882
• 质子受体: 8
• 质子供体: 6
• LogD (pH = 5.5): 8.017739
• LogD (pH = 7.4): 7.859281
• Log P: 8.019898
• 摩尔折射率: 147.612 cm^3
• 极化性: 58.13483 Å^3
• 极化表面积: 155.52 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 外观: Brown solid
• 熔点: 177–182 °C (decomposes)
• 沸点: 707°C
• 密度: 1.4 g/mL

安全信息

• 保存条件: -20°C; 2-8°C
• RTECS编号: DU3100000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-40
• 安全公开号: 22-36
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351
• GHS警示性声明: P281
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... AKR1B1(231), BAD(572), BCL2(596), LDHA(3939), LDHB(3945), MCL1(4170)

产品相关信息

• 纯度: ≥95% (HPLC)
• 成盐信息: Free Base

详细说明

MP Biomedicals - 02195210

Potential use as male contraceptive by apparently inhibiting LH.

Selleck Chemicals - S2303

Research Area: Cancer
Biological Activity:
Glycyrrhizic acid is a widely used anti-inflammatory agent isolated from the licorice root. It is metabolized to glycyrrhetic acid, which inhibits 11 beta-hydroxysteroid dehydrogenase and other enzymes involved in the metabolism of corticosteroids. Therefore, glycyrrhizic acid, which is the main and sweet component of licorice, has been investigated for its ability to cause hypermineralocorticoidism with sodium retention and potassium loss, edema, increased blood pressure, as well as depression of the renin-angiotensin-aldosterone system. [1]

Sigma Aldrich - G8761

Biochem/physiol Actions
Gossypol is a male antifertility agent and PAF antagonist/inhibitor. Gossypol is a poisonous pigment found in cottonseed and its name is derived from the botanical name of the cotton plant, Gossypium.. Gossypium is extracted from selected hybrid species between two Gossypium species, Gossypium hirsutum and Gossypium barbadens. As a PAF antagonist/inhibitor, Gossypium markedly inhibited the contractile responses of guinea pig lung parenchyma strips stimulated with leukotriene B4, seukotriene D4, and PAF-acether.

参考文献

• Poso, H., et al., Lancet , 1 : 885, (1980).
• http://en.wikipedia.org/wiki/Gossypol