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11079-53-1

Basic Information
CAS No.: 11079-53-1
Name: HYPERFORIN
Molecular Structure:
Molecular Structure of 11079-53-1 (HYPERFORIN)
Formula: C35H52O4
Molecular Weight: 536.795
Synonyms: Bicyclo[3.3.1]non-3-ene-2,9-dione,4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl)-,(1R,5S,6R,7S)- (9CI);Bicyclo[3.3.1]non-3-ene-2,9-dione,4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl)-,[1R-(6-endo,7-exo)]-;Bicyclo[3.3.1]non-3-ene-2,9-dione,4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-S-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl)-,[1R-(1a,5a,6b,7a)]-;
EINECS: 200-659-6
Density: 1.011 g/cm3
Melting Point: 79-80℃
Boiling Point: 616.825 °C at 760 mmHg
Flash Point: 340.861 °C
Appearance: White to off-white powder.
Hazard Symbols: F,T
Risk Codes: 11-23/24/25-39/23/24/25
Safety: 7-16-36/37-45
PSA: 71.44000
LogP: 8.98970
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Chemistry

Molecular Structure of Hyperforin (11079-53-1):

IUPAC Name: (1R,5R,7S,8R)-1-Butanoyl-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)bicyclo[3.3.1]non-3-ene-2,9-dione 
Molecular Formula: C35H52O4
Molecular Weight: 536.784980 g/mol
Canonical SMILES: CCCC(=O)C12C(=O)C(=C(C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C
Isomeric SMILES: CCCC(=O)[C@]12C(=O)C(=C([C@](C1=O)(C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C
InChI: InChI=1S/C35H52O4/c1-11-13-29(36)35-31(38)28(18-16-25(6)7)30(37)34(32(35)39,21-19-26(8)9)22-27(17-15-24(4)5)33(35,10)20-12-14-23(2)3/h14-16,19,27,37H,11-13,17-18,20-22H2,1-10H3/t27-,33+,34+,35-/m0/s1
InChIKey: RDEVUJPZGWFVRQ-HQKKAZOISA-N
Index of Refraction: 1.518
Molar Refractivity: 160.98 cm3
Molar Volume: 531 cm3
Surface Tension: 36.5 dyne/cm
Density: 1.01 g/cm3
Flash Point: 340.9 °C
Enthalpy of Vaporization: 104.9 kJ/mol
Boiling Point: 616.8 °C at 760 mmHg
Vapour Pressure: 8.53E-18 mmHg at 25 °C

Production

  Hyperforin (11079-53-1) can be extracted from Hypericum perforatum (St John's wort), other Hypericum species contain low amounts of hyperforin. Total synthesis of Hyperforin has not yet been accomplished, despite attempts by several research groups.

Safety Profile

Safety Information of Hyperforin (11079-53-1):
WGK Germany: 3

Specification

  Hyperforin (11079-53-1) is a prenylated phloroglucinol derivative, known as HSDB 7646 ; 4-Hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl) bicyclo(3.3.1)non-3-ene-2,9-dione ; Bicyclo(3.3.1)(1,4)benzodiazepin-5-one, 4-Hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl)-, (1R,5S,6R,7S)- . It is unstable in the presence of light and oxygen. It is active against methicillin-resistant strains of Staphylococcus aureus (MRSA) and other gram-positive bacteria.