Name: (5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
SKU: 518-28-5

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Pharmaceutical (141)
Plant Extract (49)
Others (38)
Organic Chemicals (22)
Reagent (9)
Materials (4)

Basic Information

Molecular Structure:
CAS No.:	518-28-5
Name:	(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
Article Data:	43

Formula:	C₂₂H₂₂O₈
Molecular Weight:	414.412
Synonyms:	Podophyllinic acid lactone;(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;
EINECS:	208-250-4
Density:	1.37 g/cm³
Melting Point:	183-184 °C(lit.)
Boiling Point:	597.92 °C at 760 mmHg
Flash Point:	210.181 °C
Appearance:	off-white fine crystalline powder
Hazard Symbols:	T
Risk Codes:	21-25-36/37/38-23/25-23/24/25
Safety:	36/37/39-45-26
Transport Information:	UN 3462 6.1/PG 2
PSA:	92.68000
LogP:	2.40920

Synthetic route

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

: 518-28-5
podofilox

Conditions

Conditions	Yield
With L-Selectride In tetrahydrofuran at -78℃; for 0.25h;	93%
With L-Selectride In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;	87%
With lithium tri-t-butoxyaluminum hydride In diethyl ether at -78 - 20℃; for 18h; optical yield given as %de; diastereoselective reaction;	79%
With L-Selectride In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;	70%

: 1256-91-3
(5R,6R,7R,8R)-methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate

: 518-28-5
podofilox

Conditions

Conditions	Yield
With 4 A molecular sieve; zinc(II) chloride In tetrahydrofuran at 64℃; for 2.5h;	85%
With molecular sieve; zinc(II) chloride In tetrahydrofuran	75%
With 4 A molecular sieve; zinc(II) chloride In tetrahydrofuran for 2.5h; Heating; Yield given;

: 261158-30-9
(1R,2R,3R,4R)-4-O-(2'-trimethylsilylethoxy)methylpodophyllotoxin

: 518-28-5
podofilox

Conditions

Conditions	Yield
With ethanethiol; magnesium bromide In diethyl ether; benzene at 0 - 20℃; for 11h; SEM deprotection;	81%

: 112711-16-7
(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

: 518-28-5
podofilox

Conditions

Conditions	Yield
With triethylamine hydrofluoride In acetonitrile for 72h; Ambient temperature;	79%
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	54%

: 563-80-4
3-methyl-butan-2-one

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-[(2R)-2-hydroxy-3-methylbut-2-yl]epi-podophyllotoxin

B: 7α-[(2S)-2-hydroxy-3-methylbut-2-yl]epi-podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere;	A 45% B 9% C n/a D n/a

...Expand

: 67-64-1
acetone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(2-hydroxyprop-2-yl)podophyllotoxin

B: 7β-(2-hydroxyprop-2-yl)podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; optical yield given as %de;	A 45% B 9% C n/a D n/a

...Expand

: C32H35NO8S

A: 4375-07-9
epipodophyllotoxin

B: 518-28-5
podofilox

Conditions

Conditions	Yield
With trifluoroacetic acid In tetrahydrofuran; water at 0 - 25℃; for 27h; Inert atmosphere;	A 33% B 43%
With trifluoroacetic acid In tetrahydrofuran; water at 0 - 20℃; for 24h; Overall yield = 76 %; Overall yield = 43 mg;

: 1191-95-3
cyclobutanone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 1391928-23-6
7α-(1-hydroxycyclobutyl)epi-podophyllotoxin

B: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

C: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere;	A 40% B n/a C n/a

...Expand

: 108-94-1
cyclohexanone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(1-hydroxycyclohexyl)podophyllotoxin

B: 7β-(1-hydroxycyclohexyl)podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; optical yield given as %de;	A 40% B 7% C n/a D n/a

...Expand

: 120-92-3
cyclopentanone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(1-hydroxycyclopentyl)epi-podophyllotoxin

B: 7β-(1-hydroxycyclopentyl)podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; optical yield given as %de;	A 40% B 8% C n/a D n/a

...Expand

Raw Materials

477-52-1

477-47-4

Downstream Products

477-52-1

Total:190 Page 1 of 5 1 2 3 4 5 Next>>

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Specification

The Podophyllotoxin, with CAS registry number 518-28-5, belongs to the following product categories: (1)Plant Oils, Toxins, Phenolic Acids & Derivatives; (2)Natural Plant Extract; (3)Microtobule Inhibitors; (4)Cancer Research; (5)Microtubule Inhibitors; (6)Antitumor Agents; (7)Cell Signaling and Neuroscience; (8)Cytoskeleton and Extracellular Matrix. It has the systematic name of (5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one. This chemical is a kind of off-white fine crystalline powder. And it should be stored at the temperature of 2-8°C. This chemical is exciting leads for anti-tumor agent. For instance, podophyllotoxin is the pharmacological precursor for the important anticancer drug etoposide. It is also used as a gel or solution to treat genital warts with noticeably shorter duration and fewer side effects.

Physical properties of Podophyllotoxin: (1)ACD/LogP: 2.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.345; (4)ACD/LogD (pH 7.4): 2.345; (5)ACD/BCF (pH 5.5): 35.633; (6)ACD/BCF (pH 7.4): 35.633; (7)ACD/KOC (pH 5.5): 449.188; (8)ACD/KOC (pH 7.4): 449.188; (9)#H bond acceptors: 8; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 92.68 Å²; (13)Index of Refraction: 1.606; (14)Molar Refractivity: 104.282 cm³; (15)Molar Volume: 302.394 cm³; (16)Polarizability: 41.341×10^-24cm³; (17)Surface Tension: 52.765 dyne/cm; (18)Density: 1.37 g/cm³; (19)Flash Point: 210.181 °C; (20)Enthalpy of Vaporization: 93.645 kJ/mol; (21)Boiling Point: 597.92 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by Epipodophyllotoxin. This reaction will need reagents ethanol, sodium acetate.

Uses of Podophyllotoxin: it can be used to produce 4-deoxypicropodophyllin. This reaction will need reagent H₂ and solvent acetic acid. The reaction time is 24 hour(s). The yield is about 88%.

When you are using this chemical, please be cautious about it as the following:
The Podophyllotoxin irritates to eyes, respiratory system and skin. This chemical is harmful in contact with skin. And it is toxic by inhalation, in contact with skin and if swallowed. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

You can still convert the following datas into molecular structure:
(1)SMILES: COc1cc(cc(c1OC)OC)[C@@H]2c3cc4c(cc3[C@@H]([C@@H]5[C@@H]2C(=O)OC5)O)OCO4
(2)InChI: InChI=1/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
(3)InChIKey: YJGVMLPVUAXIQN-XVVDYKMHBO
(4)Std. InChI: 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
(5)Std. InChIKey: YJGVMLPVUAXIQN-XVVDYKMHSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LD50	intramuscular	4mg/kg (4mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA SKIN AND APPENDAGES (SKIN): CUTANEOUS SENSITIZATION (EXPERIMENTAL): AFTER TOPICAL EXPOSURE	Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
cat	LD50	intravenous	1700ug/kg (1.7mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING	Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
cat	LDLo	subcutaneous	300ug/kg (0.3mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: NAUSEA OR VOMITING	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
chicken	LDLo	subcutaneous	6250ug/kg (6.25mg/kg)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
dog	LDLo	subcutaneous	1mg/kg (1mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: NAUSEA OR VOMITING	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
frog	LDLo	parenteral	152mg/kg (152mg/kg)	BEHAVIORAL: STIFFNESS	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
mouse	LD50	intraperitoneal	30mg/kg (30mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 327, 1961.
mouse	LD50	intravenous	56mg/kg (56mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01679,
mouse	LD50	oral	100mg/kg (100mg/kg)		PCT Vol. #86-04062,
mouse	LDLo	subcutaneous	24600ug/kg (24.6mg/kg)		Toxicon. Vol. 8, Pg. 85, 1970.
pigeon	LDLo	subcutaneous	10mg/kg (10mg/kg)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
rabbit	LD50	intravenous	5mg/kg (5mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA SKIN AND APPENDAGES (SKIN): CUTANEOUS SENSITIZATION (EXPERIMENTAL): AFTER TOPICAL EXPOSURE	Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
rabbit	LD50	skin	200mg/kg (200mg/kg)		PCT Vol. #86-04062,
rat	LD50	intramuscular	3mg/kg (3mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING	Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
rat	LD50	intraperitoneal	15mg/kg (15mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING	Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
rat	LD50	intravenous	8700ug/kg (8.7mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING	Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
rat	LD50	skin	500mg/kg (500mg/kg)		PCT Vol. #86-04062,
rat	LD50	subcutaneous	8mg/kg (8mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Proceedings of the Society for Experimental Biology and Medicine. Vol. 77, Pg. 269, 1951.

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Specification