477-67-8

Basic information

• Product Name: 5,6,7,8-Tetrahydro-8β-hydroxy-7α-(hydroxymethyl)-5β-(3,4,5-trimethoxyphenyl)naphtho[2,3-d]-1,3-dioxole-6α-carboxylic acid
• Synonyms: 5,6,7,8-Tetrahydro-8β-hydroxy-7α-(hydroxymethyl)-5β-(3,4,5-trimethoxyphenyl)naphtho[2,3-d]-1,3-dioxole-6α-carboxylic acid;Picropodophyllinic acid;2,3-cis-Hydroxy acid
• CAS NO: 477-67-8
• Molecular Formula: C₂₂H₂₄O₉
• Molecular Weight: 432.4206
• Mol File: 477-67-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 150-155° and 200-232°
• Boiling Point: 632.8°Cat760mmHg
• Flash Point: 220.2°C
• Appearance: /
• Density: 1.388g/cm³
• CAS DataBase Reference: 5,6,7,8-Tetrahydro-8β-hydroxy-7α-(hydroxymethyl)-5β-(3,4,5-trimethoxyphenyl)naphtho[2,3-d]-1,3-dioxole-6α-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-Tetrahydro-8β-hydroxy-7α-(hydroxymethyl)-5β-(3,4,5-trimethoxyphenyl)naphtho[2,3-d]-1,3-dioxole-6α-carboxylic acid(477-67-8)
• EPA Substance Registry System: 5,6,7,8-Tetrahydro-8β-hydroxy-7α-(hydroxymethyl)-5β-(3,4,5-trimethoxyphenyl)naphtho[2,3-d]-1,3-dioxole-6α-carboxylic acid(477-67-8)

Safety Data

• Hazardous Substances Data: 477-67-8(Hazardous Substances Data)

Upstream product

• 78216-00-9 acetyl-epipicropodophyllotoxin 
• 1180-35-4 epipodophyllotoxin acetate 
• 4375-06-8 epipicropodophyllotoxin 
• 4375-07-9 epipodophyllotoxin 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 78178-41-3 podophyllinic acid hydrazide 
• 477-47-4 picropodophyllotoxin 
• 518-28-5 podofilox 
• 79289-93-3 (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid 
• 74879-22-4 6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 42123-15-9 6-<(3,4,5-trimethoxyphenyl)methyl>benzo-1,3-dioxole-5-carboxaldehyde 
• 86301-74-8 5-Dimethoxymethyl-6-(3,4,5-trimethoxy-benzyl)-benzo[1,3]dioxole 
• 79305-58-1 (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid methyl ester 

Downstream Products

• 4375-06-8 epipicropodophyllotoxin 
• 477-47-4 (+/-)-isopodophyllotoxin 
• 477-47-4 (+/-)-epipodophyllotoxin 
• 477-47-4 (+/-)-epiisopodophyllotoxin 
• 78216-03-2 (5R,6S,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 59123-24-9 (±)-β-apopicropodophyllin 
• 171483-27-5 (5R,6S,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 171296-56-3 (-)-(1R,2S)-1,2-dihydro-1-(3,4,5-trimethoxyphenyl)-2-(hydroxymethyl)-3-formylnaphthalene 
• 199996-64-0 [(5R,6S)-7-[1,3]Dithiolan-2-yl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol 
• 199996-63-9 (5R,6S)-7-[1,3]Dithiolan-2-yl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 171483-26-4 (-)-(1R,2S)-1-(3,4,5-trimethoxyphenyl)-2-(methoxycarbonyl)-1,2-dihydro-3-naphthalenecarbaldehyde 
• 171296-48-3 (5R,6S,7R)-7-Acetoxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 477-48-5 (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione 
• 1207260-79-4 ethyl picropodophyllate 

Relevant articles and documents

New Hybrids Derived from Podophyllic Aldehyde and Diterpenylhydroquinones with Selectivity toward Osteosarcoma Cells

A new family of molecular hybrids, between cyclolignans related to podophyllic aldehyde and several diterpenylnaphthohydroquinones (DNHQ), was prepared and its biological activity evaluated in several human solid tumor cell lines, which are representative of the most prevalent solid tumors in the Western world. Both cyclolignan and quinone fragments were linked through aliphatic or aromatic spacers. The new hybrid family was evaluated for its cytotoxicity, and it was found that the hybrids were several times more potent against the osteosarcoma cell line MG-63 than against MCF-7 and HT-29 cell lines. The presence of an aromatic ring in the linker gave the most potent and selective agent, improving the cytotoxicity of the parent compounds. Cell cycle studies demonstrated that this hybrid induces a strong and rapid apoptotic effect and arrests cells at the G2/M phase of the cell cycle, in the same way that the parent compound podophyllic aldehyde does.

Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring

Several cyclolignans lacking of the Iactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the 3 aldehyde 9 (methyl 9-deoxy-9-oxo-α-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the correspnding saturated aldehyde 13 in comparison with podophyllotoxin.

Comprehensive Synthetic Route to Eight Diastereomeric Podophyllum Lignans

An oxabicyclo compound, 9, prepared in 47percent yield through an isobenzofuran intermediate was converted with excellent regio- and stereocontrol to eight (+/-)-lignan lactones of the podophyllotoxin series.One of the eight, epiisopicropodophyllin, 36, t