3162-56-9

Basic information

• Product Name: TAUREMIZINE
• Synonyms: Judaicin (eudesmane naphthofuran);TAUREMIZINE;(3S)-3aβ,5,5a,9,9aβ,9bα-Hexahydro-9-hydroxy-3β,5aα,9α-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione;(3S)-3aβ,5,5a,9,9aβ,9bα-Hexahydro-9β-hydroxy-3,5aα,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione;Barrelin;Tauremisin;Tauremizin;Vulgarin
• CAS NO: 3162-56-9
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.3169
• Mol File: 3162-56-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 240-243 °C
• Boiling Point: 449.9°Cat760mmHg
• Flash Point: 168.9°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 5.51E-10mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: ?20°C
• PKA: 13.15±0.60(Predicted)
• CAS DataBase Reference: TAUREMIZINE(CAS DataBase Reference)
• NIST Chemistry Reference: TAUREMIZINE(3162-56-9)
• EPA Substance Registry System: TAUREMIZINE(3162-56-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• WGK Germany: 3
• Hazardous Substances Data: 3162-56-9(Hazardous Substances Data)

Usage

Description

TAUREMIZINE, a sesquiterpene lactone, is a bioactive compound derived from various plant sources, particularly in the genus Vernonia. It exhibits a range of pharmacological properties, making it a potential candidate for therapeutic applications.

Uses

Used in Traditional Chinese Medicine:
TAUREMIZINE is used as a therapeutic agent for the treatment of hypertension. Its pharmacological properties contribute to the regulation of blood pressure, making it a valuable component in traditional Chinese medicine for managing this condition.

InChI:InChI=1/C15H20O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-9,11-12,18H,4,6H2,1-3H3/t8-,9-,11-,12+,14-,15+/m0/s1

Upstream product

• 67-56-1 methanol 
• 144067-18-5 Acetic acid (6Z,8Z,10E)-(3S,3aS,11aS)-3,6,10-trimethyl-2-oxo-2,3,3a,4,5,11a-hexahydro-cyclodeca[b]furan-7-yl ester 
• 72505-77-2 Peroxyvulgarin 
• 3835-53-8 (11S)-3α,4α-Epoxy-1oxoeudesmano-13,6α-lactone 
• 16886-42-3 1α-hydroxy-5α,6β,7α,11βH-eudesm-3-en-6,13-olide 
• 3650-22-4 Deoxyvulgarin 
• 66428-34-0 (11S)-3α,4α-Epoxy-1α-hydroxyeudesmano-13,6α-lactone 
• 16981-97-8 11,13-didehydrovulgarin 
• 3650-22-4 deoxyvulgarin 
• 72505-77-2 4β-Hydroperoxy-4-desoxyvulgarin 

Downstream Products

• 38236-17-8 isocostus lactone 
• 76627-95-7 Toluene-4-sulfonic acid (3S,3aS,5aR,6R,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-2-oxo-dodecahydro-naphtho[1,2-b]furan-6-yl ester 
• 66885-05-0 1-p-toluenesulfonyloxy-eudesman-3-en-6,12-olide 
• 7715-89-1 11,13-dihydrosantamarin 
• 108888-35-3 1-p-toluenesulfonyloxy-5-hydroxy-eudesman-3-en-6,12-olide 
• 122508-06-9 C₂₂H₃₀N₂O₄S 

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.

A NEW COMPONENT OF Artemisia fragrans

A new component C15H22O3, has been isolated from the epigeal part of Artemisia fragrans.On the basis of chemical transformations and spectral characteristics it has been established that it has the structure of 1α-hydroxy-5,7αH,6,11βH-eudesm-3,4-en-6,12-olide (I).

Microbial Transformations of Sesquiterpenoids: Conversion of Deoxyvulgarin by Rhizopus nigricans and Aspargillus ochraceous

Microbial transformation of the sesquiterpene lactone deoxyvulgarin (2) has been carried out with Aspergillus ochraceous and Rhizopus nigricans cultures.A. ochraceous converted deoxyvulgarin (2) into vulgarin (3) and 11,13-dihydrodouglanin (4).R. nigricans transformed deoxyvulgarin (2) into vulgarin (3), erivanin (6), and 1β-hydroxy-2-oxoeudesm-3-en-6,13-olide (7).Vulgarin (3) was obtained chemically by epoxidation of deoxyvulgarin (2) in one-step process in virtually quantitative yield.A pathway proposed for the conversion of deoxyvulgarin (2) into more functionalized metabolites is discussed.