(2R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.02,7]trideca-1(13),3,6,9,11-pentaen-5-one

• ChemBase编号: 59663
• 分子式: C18H16O7
• 平均质量: 344.31544
• 单一同位素质量: 344.08960285
• SMILES: [C@]12(c3c(c(c(c(c3O)C)O)C(=O)C)OC2=CC(=O)C(=C1O)C(=O)C)C
• Canonical SMILES: CC(=O)C1=C(O)[C@@]2(C(=CC1=O)Oc1c2c(O)c(C)c(c1C(=O)C)O)C
• InChI: InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,22-24H,1-4H3/t18-/m1/s1
• InChIKey: ICTZCAHDGHPRQR-GOSISDBHSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^2,^7]trideca-1(13),3,6,9,11-pentaen-5-one; (2R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),3,6,10,12-pentaen-5-one
• IUPAC传统名: (2R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^2,^7]trideca-1(13),3,6,9,11-pentaen-5-one; (2R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),3,6,10,12-pentaen-5-one
• 别名: (+)-Usnic acid 来源于松萝; D-2,6-二乙酰基-7,9-二羟基-8,9b-二甲基-1,3(2H,9bH)-二苯并呋喃二酮; (+)-松萝酸; (+)-松萝酸 来源于松萝; (+)-Usnic acid from Usnea dasypoga; 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3(2H,9bH)-dione; (+)-Usnic acid; (+)-Usnic acid from Usnea dasypoga; (9BR)-2,6-diacetyl-1,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-3(9bH)-one; D-Usnic acid; (+)-Usniacin(D-Usnic acid)

登记号

• CAS号: 7562-61-0
• EC号: 231-456-0
• MDL号: MFCD00016878
• Beilstein号: 96698
• PubChem SID: 162064426; 24889999; 24859825
• PubChem CID: 442614

理论计算性质

• Acid pKa: 1.3816186
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): -1.7143273
• LogD (pH = 7.4): -2.2211015
• Log P: 1.7244312
• 摩尔折射率: 90.5704 cm^3
• 极化性: 33.21925 Å^3
• 极化表面积: 121.13 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 194-204 °C; 201-203 °C(lit.)
• 比旋光度: [α]20/D +495±15°, c = 0.7% in chloroform; [α]25/D +488°, c = 0.7% in chloroform

安全信息

• 保存条件: -20°C
• 保存注意事项: IRRITANT
• RTECS编号: HP5295050
• 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
• 安全公开号: 36
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥95.0% (sum of enantiomers, TLC); 98%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C18H16O7

详细说明

Selleck Chemicals - S2252

Research Area: Infection , Neurological Disease
Biological Activity:
(+)-Usniacin(D-Usnic acid) has been found to have adrenergic activity in both frog and earthworm nerve junction models in preliminary research. It is a secondary metabolite in lichens whose role has not been completely elucidated. It is believed that usnic acid protects the lichen from adverse effects of sunlight exposure and deters grazing animals with its bitter taste. It possesses a wide range of interesting biological properties. It is a potent antibiotic effective against gram positive bacteria, including Mycobacterium tuberculosis, Staphylococcus, Streptococcus, and Pneumococcus, as well as some pathogenic fungi. It also exhibits antiviral, antiprotozoal, antimitotic, anti-inflammatory and analgesic activity.[1] has been found to have adrenergic activity in both frog and earthworm nerve junction models in preliminary research. It is a secondary metabolite in lichens whose role has not been completely elucidated. It is believed that usnic acid protects the lichen from adverse effects of sunlight exposure and deters grazing animals with its bitter taste. It possesses a wide range of interesting biological properties. It is a potent antibiotic effective against gram positive bacteria, including Mycobacterium tuberculosis, Staphylococcus, Streptococcus, and Pneumococcus, as well as some pathogenic fungi. It also exhibits antiviral, antiprotozoal, antimitotic, anti-inflammatory and analgesic activity. [1]

Sigma Aldrich - 329967

Frequently Asked Questions
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包装
5, 25 g in glass bottle

参考文献

• http://en.wikipedia.org/wiki/Usnic_acid