70477-26-8

Basic information

• Product Name: semivioxanthin
• Synonyms: semivioxanthin;(R)-3,4-Dihydro-9,10-dihydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one;(R)-Semivioxanthin
• CAS NO: 70477-26-8
• Molecular Formula: C15H14O5
• Molecular Weight: 274.26866
• Mol File: 70477-26-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 174-177℃
• Boiling Point: 496.4°Cat760mmHg
• Flash Point: 190.5°C
• Appearance: /
• Density: 1.379g/cm³
• Vapor Pressure: 1.77E-10mmHg at 25°C
• Refractive Index: 1.657
• PKA: 4.88±0.40(Predicted)
• CAS DataBase Reference: semivioxanthin(CAS DataBase Reference)
• NIST Chemistry Reference: semivioxanthin(70477-26-8)
• EPA Substance Registry System: semivioxanthin(70477-26-8)

Safety Data

• Hazardous Substances Data: 70477-26-8(Hazardous Substances Data)

Usage

Uses

(R)-Semivioxanthin is a naphthopyranone metabolite from the fungus Paecilomyces variotii.

InChI:InChI=1/C15H14O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h4-7,16-17H,3H2,1-2H3/t7-/m1/s1

Upstream product

• 330151-69-4 (R)-9-benzyloxymethoxy-3,4-dihydro-10-hydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one 
• 520-43-4 2-hydroxy-4-methoxy-6-methyl-benzoic acid methyl ester 
• 330151-68-3 methyl 2-benzyloxymethoxy-4-methoxy-6-methylbenzoate 
• 1160957-74-3 (R)-3,4-dihydro-10-hydroxy-7-methoxy-9-(2-methoxyethoxy)methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one 
• 127983-39-5 1,8-Dihydroxy-6-methoxy-3-(2-oxo-propyl)-naphthalene-2-carboxylic acid methyl ester 
• 153413-94-6 3,4-dihydro-10-hydroxy-7-methoxy-9-methoxymethoxy-3-methyl-1-oxo-1H-naphtho<2,3-c>pyran 
• 6110-37-8 methyl 2,4-dimethoxy-6-methylbenzoate 
• 153413-93-5 methyl 4-methoxy-2-(methoxymethoxy)-6-methylbenzoate 
• 127983-37-3 methyl (4,5-dihydroxy-7-methoxy-3-methoxycarbonylnaphthalen-2-yl)acetate 
• 127983-38-4 3-(3-tert-Butoxycarbonyl-2-oxo-propyl)-1,8-dihydroxy-6-methoxy-naphthalene-2-carboxylic acid methyl ester 
• 127983-36-2 1,8-Diacetoxy-6-methoxy-3-methoxycarbonylmethyl-naphthalene-2-carboxylic acid methyl ester 
• 127983-35-1 1,8-Diacetoxy-3-tert-butoxycarbonylmethyl-6-hydroxy-naphthalene-2-carboxylic acid tert-butyl ester 
• 127983-33-9 3-tert-Butoxycarbonylmethyl-1,8-dihydroxy-6-(2-hydroxymethyl-benzyloxy)-naphthalene-2-carboxylic acid tert-butyl ester 
• 127983-34-0 1,8-Diacetoxy-6-(2-acetoxymethyl-benzyloxy)-3-tert-butoxycarbonylmethyl-naphthalene-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

New naphthopyranone glycosides from Paepalanthus vellozioides and Paepalanthus latipes

Three new compounds - 3,4-dihydro-10-hydroxy-7-methoxy-3-(R)-methyl-1H- 3,4-dihydronaphtho-]2,3c]-pyran-1-one-9-O-β-D-glucopyranoside (1), 3,4- dihydro-10-hydroxy-7-methoxy-3-(R)-methyl-1H-3,4-dihydronaphtho-[2,3c]- pyran-1-one-9-O-β-D-glucopyranosyl-(1→6)-glucopyranoside (2), and 3,4- dihydro-10-dihydroxy-7-methoxy-3-(R)-methyl-1H-3,4-dihydronaphtho-[2,3c]- pyran-1-one-9-O-β-D-allopyranosyl (1→6) glucopyranoside (3) - were isolated from the leaves of Paepalanthus vellozioides and Paepalanthus latipes and characterized by spectrometric methods, mainly electrospray mass spectrometry and 1D and 2D NMR experiments. These unusual glycosylated dihydronaphthopyranones may serve as taxonomic markers of the genus Paepalanthus, since these compounds were not detected in other genera belonging to the Eriocaulaceae family.

Total synthesis of (R)- and (S)-semi-vioxanthin

Compounds (R)- and (S)-semi-vioxanthin 2 were synthesized by a tandem Michael reaction of orsellinate 3 and the chiral Michael acceptors 4. The key step for the formation of lactone (R)-4. is a regio- and enantioselective, enzyme-catalyzed reduction of tert-butyl 3,5-dioxohexanoate (5) by an alcoholdehydrogenase from Lactobacillus brevis. Compound (S)-4 was synthesized by the Claisen condensation of tert-butyl acetate and ethyl (S)-3-hydroxy-butanoate (8). Cleavage of the benzyloxymethyl groups in the protected (R)- and (S)-semi-vioxanthins was achieved by hydrogenolysis to afford (R)-2 and (S)-2, respectively.

Synthesis of Semivioxanthin via a Polyketide

The first synthesis of semivioxanthin has been achieved via the intermediate 3,5,7,9,11-pentaoxo-tridecanedioate one of whose ketone groups was protected as a ketal of o-phenylenedimethanol.