(3aS,9aS,9bS)-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

• ChemBase编号: 154820
• 分子式: C15H16O3
• 平均质量: 244.28574
• 单一同位素质量: 244.10994437
• SMILES: CC1=C2[C@@H]([C@@H]3[C@@H](CC1)C(=C)C(=O)O3)C(=CC2=O)C
• Canonical SMILES: CC1=CC(=O)C2=C(C)CC[C@@H]3[C@@H]([C@@H]12)OC(=O)C3=C
• InChI: InChI=1S/C15H16O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,10,13-14H,3-5H2,1-2H3/t10-,13-,14-/m0/s1
• InChIKey: SKNVIAFTENCNGB-BPNCWPANSA-N

名称和登记号

名称

• IUPAC标准名: (3aS,9aS,9bS)-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione
• IUPAC传统名: (3aS,9aS,9bS)-6,9-dimethyl-3-methylidene-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione
• 别名: 11,13-Dehydroleucodin; Dehydroleucodin; Leucodin; Lidbeckialactone; Mesatlantin E; NSC 180034; [3aS-(3aalpha,9aalpha,9bbeta)]-3,3a,4,5,9a,9b-hexahydro-6,9-dimethyl-3-methylene-azuleno[4,5-b]furan-2,7-dione; dehydro-; Dehydroleucodine

登记号

• CAS号: 36150-07-9
• MDL号: MFCD06794926
• PubChem SID: 162248958
• PubChem CID: 73440

理论计算性质

• Acid pKa: 15.133956
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 2.6081917
• LogD (pH = 7.4): 2.6081917
• Log P: 2.6081917
• 摩尔折射率: 68.5197 cm^3
• 极化性: 26.285416 Å^3
• 极化表面积: 43.37 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: ≥30 mg/mL
• 外观: white to off-white powder

安全信息

• 保存条件: desiccated; protect from light; under inert gas
• 德国WGK号: 3
• 保存温度: room temp

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H16O3

详细说明

Sigma Aldrich - D4196

Biochem/physiol Actions
Dehydroleucodine is a sesquiterpene lactone isolated from Artemisia douglasiana Besser; mast cell stabilizers. An extract from the plant is widely used in Cuyo region (Argentina) as folk medicine for the treatment of gastric ailments. The compound prevents gastric and duodenal damages in response to necrosis-inducing agents. Stabilization of mast cells may be a key mechanism to protect the gastrointestinal tract from injury and ulceration. Recently, it was established that dehydroleucodine and xanthatin inhibit mast cell degranulation induced by compound 48/80.