22733-60-4

Basic information

• Product Name: Siccanin
• Synonyms: Siccanin;1,2,3,4,4a,5,6,6a,11b,13b-Decahydro-4,4,6a,9-tetramethyl-13H-benzo[a]furo[2,3,4-mn]xanthen-11-ol;13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol, 1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl- (8CI);13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol, 1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl-, (4aS,6aS,11bR,13aS,13bS)- (9CI);13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol, 1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl-, [4aS-(4aa,6aa,11ba,13aR*,13ba)]-;NSC 135048;(13As)-1,2,3,4,4abeta,5,6,6A,11bbeta,13bbeta-decahydro-4,4,6abeta,9-tetramethyl-13H-benzo(A)furo(2,3,4-mn)xanthen-11-ol;13H-Benzo(A)furo(2,3,4-mn)xanthen-11-ol, 1,2,3,4,4A,5,6,6A,11B,13B-decahydro-4,4,6A,9-tetramethyl-, (4as-(4aalpha,6aalpha,11balpha,13ar*,13balpha))-
• CAS NO: 22733-60-4
• Molecular Formula: C22H30O3
• Molecular Weight: 342.476
• Mol File: 22733-60-4.mol

Chemical Properties

• Melting Point: 139-140°
• Boiling Point: 427.8°Cat760mmHg
• Flash Point: 212.5°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 6.41E-08mmHg at 25°C
• Refractive Index: 1.593
• PKA: 10.9(at 25℃)
• CAS DataBase Reference: Siccanin(CAS DataBase Reference)
• NIST Chemistry Reference: Siccanin(22733-60-4)
• EPA Substance Registry System: Siccanin(22733-60-4)

Safety Data

• Hazardous Substances Data: 22733-60-4(Hazardous Substances Data)

Usage

Uses

Used in Antifungal Applications:
Siccanin is used as an antifungal agent for inhibiting the growth of various fungal species, such as T. mentagrophytes and C. albicans strains. It achieves this by inhibiting succinate oxidation in the mitochondria, with IC50 values ranging from 0.3 μg/ml to 90 μg/ml depending on the species and growth conditions.
Used in Drug Development:
Siccanin is used as a lead compound in the development of new chemotherapeutics due to its unique species-selective inhibition of succinate dehydrogenase. Its proximity to the quinone-binding site of the enzyme offers potential for designing more effective and targeted treatments.
Used in Research:
Siccanin is used in research to study the function and inhibition of succinate dehydrogenase in the terminal electron transport system. Its unique binding properties provide valuable insights into the development of novel inhibitors and understanding the underlying mechanisms of action.

InChI:InChI=1/C22H30O3/c1-13-10-14(23)17-15(11-13)25-21(4)9-6-16-20(2,3)7-5-8-22(16)12-24-18(17)19(21)22/h10-11,16,18-19,23H,5-9,12H2,1-4H3/t16?,18-,19?,21?,22?/m0/s1

Upstream product

• 35477-60-2 (-)-siccanin methyl ether 
• 618120-21-1 (-)-siccanochromene methyl ether 
• 166022-29-3 (S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol 
• 502763-34-0 (S)-1-[1′-benzenesulfonyl]methyl-2,2-dimehtyl-6-methylenecyclohexane 
• 35477-60-2 siccanochromene E methyl ether 
• 78412-85-8 8aα-methoxymethyl-5,5-dimethyl-4aα,5,6,7,8,8a-hexahydro-2(1H)-naphthalenone 
• 78310-24-4 8a-methoxymethyl-5,5-dimethyl-1,5,6,7,8,8a-hexahydro-2(3H)-naphthalenone 
• 78310-22-2 8a-hydroxymethyl-5,5-dimethyl-1,5,6,7,8,8a-hexahydro-2(3H)-naphthalenone 2-ethylene acetal 
• 78310-21-1 8a-carbomethoxy-5,5-dimethyl-1,5,6,7,8,8a-hexahydro-2(3H)-naphthalenone 2-ethylene acetal 
• 78310-25-5 1ξ-hydroxymethyl-8aα-methoxymethyl-5,5-dimethyl-4aα,5,6,7,8,8a-hexahydro-2(1H)-naphthalenone 
• 78310-27-7 1ξ-hydroxymethyl-8aα-methoxymethyl-5,5-dimethyl-3,4,4aα,5,6,7,8,8a-octahydro-2H(1H)-naphthalenone 
• 78310-19-7 4a-carbomethoxy-1,1-dimethyl-3,4,4a,5-tetrahydronaphthalene-2,6(1H,7H)-dione 6-ethylene acetal 
• 78310-34-6 (1R,2R,4aS,8aS)-1-[(2,6-Dimethoxy-4-methyl-phenyl)-hydroxy-methyl]-8a-methoxymethyl-2,5,5-trimethyl-decahydro-naphthalen-2-ol 
• 78310-20-0 C₂₃H₃₀N₂O₆S 

Relevant articles and documents

Biomimetic enantioselective total synthesis of (-)-siccanin via the Pd-catalyzed asymmetric allylic alkylation (AAA) and sequential radical cyclizations

(-)-Siccanin (1), a natural product possessing significant antifungal properties, was synthesized enantioselectively via a biomimetic route. This synthetic route features two sequential radical cyclizations: a Ti(III)-mediated radical cyclization of epoxy

An enantioselective biomimetic total synthesis of (-)-siccanin

A convergent asymmetric synthesis of the clinically important antifungal agent (-)-siccanin (1) mimics the proposed biosynthetic pathway. A Pd-catalyzed asymmetric allylic alkylation was used to establish the stereochemistry, and sequential radical proces

Total Synthesis of dl-Siccanin and dl-Siccanochromene E

The stereoselective synthesis of dl-siccanin (1) and dl-siccanochromene E (2) has been described.Acid isomerization of nonconjugated octalone 11a, derived from known octalone 5, stereoselectively provided cis-fused octalone 12, from which cis-drimane alde