103548-82-9

Basic information

• Product Name: Huperzine B
• Synonyms: HuperzineB;12-Methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-prop[1]eno-1,7-phenanthrolin-8(7H)-one;8,15-Didehydrolycodin-1(18H)-one
• CAS NO: 103548-82-9
• Molecular Formula: C₁₆H₂₀N₂O
• Molecular Weight: 256.347
• Product Categories: reference substance
• Mol File: 103548-82-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 533.5 °C at 760 mmHg
• Flash Point: 216.4 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 1.84E-11mmHg at 25°C
• Refractive Index: 1.623
• PKA: 12.92±0.40(Predicted)
• CAS DataBase Reference: Huperzine B(CAS DataBase Reference)
• NIST Chemistry Reference: Huperzine B(103548-82-9)
• EPA Substance Registry System: Huperzine B(103548-82-9)

Safety Data

• Hazardous Substances Data: 103548-82-9(Hazardous Substances Data)

Usage

Uses

Huperzine B is a plant-derived alkaloid displaying anti-cholinesterase activity.

InChI:InChI=1/C16H20N2O/c1-10-7-11-8-14-13(4-5-15(19)18-14)16(9-10)12(11)3-2-6-17-16/h4-5,7,11-12,17H,2-3,6,8-9H2,1H3,(H,18,19)/t11-,12+,16-/m0/s1

Upstream product

• 1510775-88-8 (5R,10bR)-12-methyl-2,3,5,6-tetrahydro-1H-5,10b-prop[1]eno-1,7-phenanthrolin-8(7H)-one 
• 1510775-59-3 tert-butyl ((5S,9S,11S)-11-allyl-11-hydroxy-2-methoxy-7-methyl-5,8,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate 
• 1391435-96-3 C₁₉H₂₄N₂O₄ 
• 1510775-61-7 tert-butyl ((5S,9S,11R)-11-allyl-11-hydroxy-2-methoxy-7-methyl-5,8,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate 
• 89-82-7 pulegone 
• 1393110-52-5 C₈H₉F₃O₄S 
• 1510775-66-2 tert-butyl ((5S,9S,11S)-11-hydroxy-11-(3-hydroxypropyl)-2-methoxy-7-methyl-5,8,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate 
• 1393110-49-0 C₁₂H₁₉NO₃ 
• 156094-64-3 2-(bromomethyl)-3-bromo-6-methoxypyridine 
• 1391436-01-3 C₁₉H₂₅BrN₂O₄ 
• 1510775-71-9 (4aS,5S,10bS)-8-methoxy-12-methyl-2,3,4,4a,5,6-hexahydro-1H-10b,5-prop[1]eno-1,7-phenanthrolin-4a-ol 
• 1510775-78-6 tert-butyl ((5S,9S,11R)-11-hydroxy-11-(3-hydroxypropyl)-2-methoxy-7-methyl-5,8,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate 
• 1510775-81-1 (4aR,5S,10bS)-8-methoxy-12-methyl-2,3,4,4a,5,6-hexahydro-1H-10b,5-prop[1]eno-1,7-phenanthrolin-4a-ol 

Downstream Products

• 110037-64-4 N-methylhuperzine B 
• 847776-51-6 C₃₀H₃₈N₄O₃ 
• 847776-49-2 C₂₉H₃₆N₄O₂ 
• 847776-56-1 C₃₁H₃₃N₃O₂ 
• 847776-62-9 C₂₈H₃₅N₃O₂ 
• 847776-60-7 C₂₇H₃₃N₃O₂ 
• 847776-58-3 C₂₆H₃₁N₃O₂ 
• 612-60-2 7-methylquinoline 
• 3279-76-3 6-methyl-2(1H)-pyridone 

Relevant articles and documents

Divergent total synthesis of the lycopodium alkaloids huperzine A, huperzine B, and huperzine U

Huperzine A, huperzine B, and huperzine U are congeners isolated from the Chinese herb Huperzia serrata (=Lycopodium serratum) in minuscule amounts. The most efficient total synthesis of huperzine A, the first asymmetric total syntheses of huperzine B, and the first total synthesis of huperzine U have been achieved efficiently in overall yields of 17%, 10%, and 9%, respectively, each spanning 10-13 steps from (R)-pulegone. The featured steps include palladium-catalyzed Buchwald-Hartwig coupling and Heck cyclization reactions and an Ir-catalyzed olefin isomerization reaction. This work has established the absolute configurations of huperzine B and huperzine U and revealed that natural huperzine A, huperzine B, and huperzine U possess the same set of absolute stereochemistries, thus providing support for the potential role of huperzine B and huperzine U in the biosynthesis of huperzine A.