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Merck
CN

73379

Podophyllotoxin

analytical standard

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About This Item

Empirical Formula (Hill Notation):
C22H22O8
CAS Number:
518-28-5
Molecular Weight:
414.41
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329764848
EC Number:
208-250-4
Beilstein/REAXYS Number:
99163
MDL number:
MFCD00075290

Key Documents

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InChI key

YJGVMLPVUAXIQN-XVVDYKMHSA-N

InChI

1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

SMILES string

COc1cc(cc(OC)c1OC)[C@H]2C3C(COC3=O)[C@@H](O)c4cc5OCOc5cc24

grade

analytical standard

assay

≥98.0% (HPLC)

optical activity

[α]/D 131±2°, c = 1 in chloroform

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

mp

183-184 °C (lit.)

format

neat

storage temp.

2-8°C

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Inhibits microtubule assembly; antineoplastic.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW5492
BCBV2828
BCBV2572

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Anita Kumari et al.
BMC genomics, 15, 871-871 (2014-10-08)
Sinopodophyllum hexandrum is an endangered medicinal herb, which is commonly present in elevations ranging between 2,400-4,500 m and is sensitive to temperature. Medicinal property of the species is attributed to the presence of podophyllotoxin in the rhizome tissue. The present work
Charles L Cantrell et al.
PloS one, 9(9), e106057-e106057 (2014-09-10)
Juniperus horizontalis Moench (Family Cupressaceae), commonly called creeping juniper, is a widely distributed species in the United States and much of Canada. It is potentially a source for two important chemical products, the anticancer drug synthetic precursor, podophyllotoxin and essential
Wendy Itzel Escobedo Hinojosa et al.
Journal of ethnopharmacology, 155(2), 1156-1163 (2014-06-28)
The root barks of Hippocratea celastroides have been used for decades in Mexican traditional medicine to treat gastritis and ulcers. To investigate the anti-Helicobacter pylori, gastroprotective, anti-inflammatory, and cytotoxic activities of methanolic extracts obtained from the leaves, stems, and root
Marek Och et al.
Pharmaceutical biology, 53(6), 831-837 (2015-02-28)
The demand for podophyllotoxin and deoxypodophyllotoxin is still increasing and commercially exploitable sources are few and one of them, Podophyllum hexandrum Royle (Berberidaceae), is a "critically endangered" species. The first aim was to quantify the amount of podophyllotoxin and deoxypodophyllotoxin
Cheng-Ting Zi et al.
Bioorganic & medicinal chemistry, 23(7), 1437-1446 (2015-03-07)
A series of perbutyrylated glycosides of podophyllotoxin and its derivatives were synthesized and evaluated for their antitumor activity in vitro. Most of them exhibit cytotoxic activity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480)
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