4'-Demethylepipodophyllotoxin - ≥98% , CAS No.6559-91-7

CAS: 6559-91-7 Cat. No.: D276525 Molecular Weight: 400.38 EC Number: 613-823-0

GRADE & PURITY ≥98%

Synonyms

(5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one | Tox21_113196 | 4'-O-demethylepipodophyllotoxin | A935071 | 4'-demethyl-9-epipodophyllotoxin | D5653 | CYANOCOBALAMIN COMPONENT

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

(5S, 5aR, 8aR, 9R)-5-hydroxy-9-(4-hydroxy-3, 5-dimethoxy-phenyl)-5a, 6, 8a, 9-tetrahydro-5H-isobenzofuro[6, 5-f][1, 3]benzodioxol-8-one | Tox21_113196 | 4'-O-demethylepipodophyllotoxin | A935071 | 4'-demethyl-9-epipodophyllotoxin | D5653 | CYANOCOBALAMIN COMPONENT

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Antimitotic agent. Potent inhibitor of microtubule assembly. Antioxidant and chemopreventive effects in vivo. Orally active.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488187688
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187688
• Canonical Smiles: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
• IUPAC Name: (5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• InChIKey: YVCVYCSAAZQOJI-JHQYFNNDSA-N
• INCHI: 1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O
• Molecular Weight: 400.38
• Reaxy-Rn: 365236
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=365236&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lignans, neolignans and related compounds
    • Class Lignan lactones
      • Subclass Podophyllotoxins

• Kingdom: Organic compounds
• Superclass: Lignans, neolignans and related compounds
• Class: Lignan lactones
• Subclass: Podophyllotoxins
• Intermediate Tree Nodes: Not available
• Direct Parent: Podophyllotoxins
• Alternative Parents: Aryltetralin lignans Furanonaphthodioxoles Tetralins Dimethoxybenzenes Methoxyphenols Benzodioxoles Anisoles Phenoxy compounds Alkyl aryl ethers Gamma butyrolactones Tetrahydrofurans Carboxylic acid esters Secondary alcohols Monocarboxylic acids and derivatives Oxacyclic compounds Acetals Hydrocarbon derivatives Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Podophyllotoxin - 1-aryltetralin lignan - Linear furanonaphthodioxole - Naphthofuran - Methoxyphenol - M-dimethoxybenzene - Dimethoxybenzene - Tetralin - Benzodioxole - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Alkyl aryl ether - Phenol - Benzenoid - Gamma butyrolactone - Monocyclic benzene moiety - Tetrahydrofuran - Lactone - Carboxylic acid ester - Secondary alcohol - Acetal - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Ether - Monocarboxylic acid or derivatives - Alcohol - Carbonyl group - Organic oxygen compound - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).
• External Descriptors: organic heterotetracyclic compound - phenols - furonaphthodioxole

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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HL-60 (67320 Activities)

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HT-1080 (3966 Activities)

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HT-29 (80576 Activities)

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MCF7 (126967 Activities)

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MRC5 (9203 Activities)

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A549 (127892 Activities)

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H9 (1832 Activities)

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HaCaT (4069 Activities)

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HMEC (560 Activities)

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HepG2 (196354 Activities)

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KB (17409 Activities)

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M21 (1715 Activities)

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HeLa (62764 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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Associated Targets(non-human)

Top2 DNA topoisomerase II (15 Activities)

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Human alphaherpesvirus 1 (11089 Activities)

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BCHE Cholinesterase (8742 Activities)

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Mythimna separata (3306 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (with warming)；Chloroform (Slightly), Methanol (Slightly)
• Sensitivity: Heat Sensitive
• Specific Rotation[α]: -68.0 to -60.0 deg(C=0.65, MeOH)
• Melt Point(°C): 220-225ºC
• Molecular Weight: 400.400 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 400.116 Da
• Monoisotopic Mass: 400.116 Da
• Topological Polar Surface Area: 104.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 614.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xiang Zhou, Haojie Ye, Xiuhui Gao, Yumei Feng, Wubin Shao, Puying Qi, Zhibing Wu, Liwei Liu, Peiyi Wang, Song Yang.  (2021)  The discovery of natural 4'-demethylepipodophyllotoxin from renewable Dysosma versipellis species as a novel bacterial cell division inhibitor for controlling intractable diseases in rice.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2021.114182]