518-29-6

Basic information

• Product Name: PELTATIN
• Synonyms: PELTATIN;(5R)-5,8,8aβ,9-Tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aαH)-one;β-Peltatin A;b-Peltatin
• CAS NO: 518-29-6
• Molecular Formula: C₂₂H₂₂O₈
• Molecular Weight: 414.40528
• Mol File: 518-29-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 234 °C
• Boiling Point: 586.8°Cat760mmHg
• Flash Point: 205.8°C
• Appearance: /
• Density: 1.363g/cm³
• PKA: 9.49±0.40(Predicted)
• CAS DataBase Reference: PELTATIN(CAS DataBase Reference)
• NIST Chemistry Reference: PELTATIN(518-29-6)
• EPA Substance Registry System: PELTATIN(518-29-6)

Safety Data

• Hazardous Substances Data: 518-29-6(Hazardous Substances Data)

Usage

Uses

β-Peltatin is one of the major lignans in Podophyllum peltatum, and is one of the components of Podophyllin, a complex mixture of oils and pigments that was used as a purgative. β-Peltatin also has biological activity against tumours.

Definition

ChEBI: An organic heterotetracyclic compound that is alpha-peltatin in which the phenolic hydroxy group of the 4-hydroxy-3,5-dimethoxyphenyl substitutent had been converted to the corresponding methyl ether.

Upstream product

• 477-51-0 deoxypodophyllotoxin 
• 82299-45-4 (5aR,8aR)-10-Benzyloxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 82299-37-4 benzyloxy-2 piperonal 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 69393-72-2 2H-benzo[d][1,3]dioxolan-4-ol 
• 82299-36-3 bromo-5 hydroxy-4 benzodioxole-1,3 
• 23780-59-8 4-hydroxybenzo[d][1,3]dioxole-5-carbaldehyde 
• 82299-40-9 (hydroxy-2 methylenedioxy-3,4 benzyl)-4 dihydro-3H-furannone-2 
• 82299-41-0 (benzyloxy-2 methylenedioxy-3,4 benzyl)-4 dihydro-3H-furannone-2 
• 82299-39-6 (benzyloxy-2 methylenedioxy-3,4 benzylidene)-4 dihydro-3H-furannone-2 
• 82299-38-5 acide (benzyloxy-2 methylenedioxy-3,4 phenyl)-4 methoxycarbonyl-3 butene-3 oique 
• 82314-35-0 (5aS,8aR)-10-Benzyloxy-5-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 82299-45-4 O-benzyl (+/-)-iso-β-peltatine 

Downstream Products

• 23978-65-6 (-)-β-peltatin-A-methyl ether 
• 50905-47-0 O-Acetyl-β-peltatin-B 
• 119906-98-8 O-Acetyl-β-peltatin-A 
• 641-25-8 β-Peltatin-B 
• 71654-65-4 8-O-(Hepta-O-acetyl-cellobiosyl)-β-peltatin-A 
• 71623-55-7 8-O-(β-Cellobiosyl)-β-peltatin-A 
• 38943-35-0 β-peltatin B methyl ether 

Relevant articles and documents

Aryltetralin-lignan formation in two different cell suspension cultures of Linum album: Deoxypodophyllotoxin 6-hydroxylase, a key enzyme for the formation of 6-methoxypodophyllotoxin

Suspension cultures initiated from two different Linum album seedlings accumulate either podophyllotoxin (PTOX, 2.6 mg/g DW) or 6-methoxypodophyllotoxin (6MPTOX, 5.4 mg/g DW) as main lignans. Two molecules of coniferyl alcohol are dimerized to pinoresinol which is converted via several steps into deoxypodophyllotoxin (DOP) which seems to be the branching point to PTOX or 6MPTOX biosynthesis. DOP is hydroxylated at position 7 to give PTOX by deoxypodophyllotoxin 7-hydroxylase (DOP7H). In contrast, 6MPTOX biosynthesis is achieved by DOP hydroxylation at position 6 to β-peltatin by the cytochrome P450 enzyme deoxypodophyllotoxin 6-hydroxylase (DOP6H). The following methylation to β-peltatin-A-methylether is catalyzed by β-peltatin 6-O-methyltransferase (βP6OMT) from which 6MPTOX is formed by hydroxylation at position 7 by β-peltatin-A-methylether 7-hydroxylase (PAM7H). DOP6H and βP6OMT could be characterized in protein extracts from cell cultures of L. flavum and L. nodiflorum, respectively, and here in L. album for the first time. DOP7H and PAM7H activities could not yet be detected with protein extracts. Experiments of feeding DOP together with inhibitors of cytochrome P450 depending as well as dioxygenase enzymes were performed in order to shed light on the type of DOP7H and PAM7H. Growth parameters and specific activities of enzymes from the phenylpropane as well as the lignan specific biosynthetic pathway were measured during a culture period of 16 days. From the enzymes studied only the DOP6H showed a differential activity sustaining the hypothesis that this enzyme is responsible for the differential lignan accumulation in both cell lines.

SYNTHESE TOTALES DE LA (+/-) ISO β-PELTATINE ET DE SES ANALOGUES

α-Hydroxyalkylation of a β-(2-alkoxy 3,4-methylenedioxy benzyl)-γ-butyrolactone (17 or 25) with 3,4,5-trimethoxybenzaldehyde or syringaldehyde 27, followed by cyclisation, afforded good yields of the corresponding (+/-) isopeltatins.