17237-80-8

Basic information

• Product Name: (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3a,5,5a,9,9a,9b-hexahydronaphtho[1,2-b]furan-2,6(3H,4H)-dione
• Synonyms: (3S,3aS,5aR,9R,9aS,9bS)-9-Hydroxy-3,5a,9-trimethyl-3a,5,5a,9,9a,9b-hexahydronaphtho[1,2-b]furan-2,6(3H,4H)-dione; naphtho[1,2-b]furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, (3aS,5aR,9R,9aS,9bS)-; naphtho[1,2-b]furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, (3S,3aS,5aR,9R,9aS,9bS)-
• CAS NO: 17237-80-8
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.3169
• Mol File: 17237-80-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 449.9°C at 760 mmHg
• Flash Point: 168.9°C
• Density: 1.2g/cm³
• Vapor Pressure: 5.51E-10mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3a,5,5a,9,9a,9b-hexahydronaphtho[1,2-b]furan-2,6(3H,4H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3a,5,5a,9,9a,9b-hexahydronaphtho[1,2-b]furan-2,6(3H,4H)-dione(17237-80-8)
• EPA Substance Registry System: (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3a,5,5a,9,9a,9b-hexahydronaphtho[1,2-b]furan-2,6(3H,4H)-dione(17237-80-8)

Safety Data

• Hazardous Substances Data: 17237-80-8(Hazardous Substances Data)

Upstream product

• 16981-97-8 11,13-didehydrovulgarin 
• 72505-77-2 4β-Hydroperoxy-4-desoxyvulgarin 
• 3650-22-4 deoxyvulgarin 
• 481-06-1 santonin 
• 1618-78-6 6-epi-α-Santonin 
• 14794-68-4 3-Oxo-5,6αH,4,11βH-eudesman-12,6-olide 
• 4678-03-9 (3S,3aS,5aS,9S,9aS,9bR)-8-Hydroxy-3,5a,9-trimethyl-3a,4,5,5a,8,9,9a,9b-octahydro-3H-naphtho[1,2-b]furan-2-one 
• 6089-71-0 (3S,3aS,5aS,9S,9aS,9bR)-8-Hydroxy-3,5a,9-trimethyl-decahydro-naphtho[1,2-b]furan-2-one 
• 66260-88-6 3β,4β-epoxy-1,1-ethylenedioxy-5,6αH,11βH-eudesman-6,12-olide 
• 132294-82-7 1,1-ethylenedioxy-5,6αH,4,11βH-eudesm-3-en-6,12-olide 
• 132294-81-6 1α,2α-epoxy-3-oxo-5,6αH,4,11βH-eudesman-6,12-olide 
• 132185-39-8 1-oxo-5,6αH,4,11βH-eudesm-2-en-6,12-olide 
• 132204-36-5 2α-bromo-3-oxo-5,6αH,4,11βH-eudesman-6,12-olide 
• 132185-35-4 11,13-dihydro-6β-tuberiferin 

Downstream Products

• 132185-41-2 6β-vulgarin 
• 7715-89-1 11,13-dihydrosantamarin 

Relevant articles and documents

Transformations of Some Sesquiterpene Lactones by Filamentous Fungi and Cytotoxic Evaluations

Biotransformation is an economically and ecologically viable technology which has been used to modify the structures of many classes of biologically active products. Some fungi may be useful for the biotransformation of sesquiterpene lactones (SLs), leading to unusual structural changes that modify their biological activities, and other transformations mimic their biosynthetic pathways, generating evidences for the proposed biogenesis. Eight filamentous fungi were screened for their ability to transform different SLs (1?–?9), and microbial reactions yielded compounds 10?–?17, which in turn have been isolated as natural products, thus mimicking their biosynthesis. Their structures were identified based on NMR and MS spectroscopic analyses. The cytotoxicities of SLs 1, 4, 6, 7 and 9, and their biotransformed produts (10, 14, 15 and 17) against human cancer cell lines U251 (glia), PC3 (prostate), K562 (leukemia), HCT-15 (colon), MCF7 (breast), and SKLU-1 (lung), were determined, confirming that the presence of Michael acceptor is an important feature for the bioactivity.

SYNTHESIS, BIOTRANSFORMATION AND STEREOCHEMISTRY OF 6β-SESQUITERPENE LACTONES: SYNTHESES OF 6β-ARTEPAULIN, 11,13-DIHYDRO-6β-TUBERIFERIN, 5,15-DIHYDRO-6β-OOPODIN, 4-EPI-6β-VULGARIN AND 6β-VULGARIN

6β-Artepaulin, 11,13-dihydro-6β-tuberiferin, 4,15-dihydro-6β-oopodin, 4-epi-6β-vulgarin and 6β-vulgarin were obtained from α-santonin.Stereochemical studies showed that the configuration at C-6 is decisive in the chemical behaviour of the A ring.Biotransformation of 1-oxo-5,6α,4,11βH-eudesm-2-en-6,12-olide with Rhizopus nigricans cultures probed to be a very efficient alternative way to obtain 4-epi-6β-vulgarin, which was then converted to 6β-vulgarin, a convenient starting material for biogenetical studies of pseudoguaianolides.A new 8β-hydroxyl derivative obtained from this biotransformation constitutes a new approach to the synthesis of 8,12-eudesmanolides and other sesquiterpenolides.Molecular structures were determined mainly by mono- and bidimensional nmr experiments.

BIOGENETIC-TYPE SYNTHESIS OF VULGARIN AND PEROXYVULGARIN

The eudesmanolides vulgarin and peroxyvulgarin were obtained via a biogenetic-type route that involved photo-oxygenation of 1-oxo-5αH,6,11βH-eudesm-3-en-6,12-olide.The α-face singlet oxygen (1O2) attack resulted in the production of peroxyvulgarin as the major product.Stannous chloride reduction of that compound readily yielded vulgarin.These two compounds, vulgarin and peroxyvulgarin, were isolated from Artemisia abyssinica.Key Word Index- Artemisia abyssinica; Compositae; vulgarin; peroxyvulgarin; photo-oxygenation; biogenetic; 1-oxo-5αH,6,11βH-eudesm-3-en-6,12-olide.