(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 ID: 59663
• Molecular Formular: C18H16O7
• Molecular Mass: 344.31544
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: (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
• Synonyms: (+)-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); (+)-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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 1.3816186
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.7143273
• LogD (pH = 7.4): -2.2211015
• Log P: 1.7244312
• Molar Refractivity: 90.5704 cm^3
• Polarizability: 33.21925 Å^3
• Polar Surface Area: 121.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• RTECS: HP5295050
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (sum of enantiomers, TLC); 98%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H16O7

DETAILS

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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Packaging
5, 25 g in glass bottle

REFERENCES

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