20-Deoxyingenol

CAS# 54706-99-9

20-Deoxyingenol

Catalog No. BCN3770----Order now to get a substantial discount!

Product Name & Size Price Stock
20-Deoxyingenol: 5mg $173 In Stock
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Quality Control of 20-Deoxyingenol

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Chemical structure

20-Deoxyingenol

3D structure

Chemical Properties of 20-Deoxyingenol

Cas No. 54706-99-9 SDF Download SDF
PubChem ID 11290503 Appearance Powder
Formula C20H28O4 M.Wt 332.4
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility DMSO : 50 mg/mL (150.41 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name (1S,4S,5S,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-3,7,11,11,14-pentamethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
SMILES CC1CC2C(C2(C)C)C3C=C(C(C4(C1(C3=O)C=C(C4O)C)O)O)C
Standard InChIKey FOSYZKSOJUQLTD-NHPMXQBPSA-N
Standard InChI InChI=1S/C20H28O4/c1-9-6-12-14-13(18(14,4)5)7-11(3)19(17(12)23)8-10(2)16(22)20(19,24)15(9)21/h6,8,11-16,21-22,24H,7H2,1-5H3/t11-,12+,13-,14+,15-,16+,19+,20+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 20-Deoxyingenol

The seeds of Euphorbia lathyris L.

Biological Activity of 20-Deoxyingenol

DescriptionStandard reference
In vitro

Diterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of Xenopus (part 2).[Pubmed: 12913231]

Chem Pharm Bull (Tokyo). 2003 Aug;51(8):935-41.


METHODS AND RESULTS:
Four new ingenane-type diterpenes, 3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-O-acetylingenol (1), 3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-Deoxyingenol (2), 3-O-(2E,4Z-decadienoyl)-20-Deoxyingenol (3), and 3-O-(2E,4E-decadienoyl)-20-Deoxyingenol (4), two new jatrophane-type diterpenes, kansuinins D (9) and E (10), and four known ingenane-type diterpenes were isolated from the root of Euphorbia kansui. Their structures were elucidated by spectroscopic and chemical analysis, and individual Xenopus cells at the blastular stage were cultured with the diterpenes to test for biological activity.
CONCLUSIONS:
20-Deoxyingenol diterpenes 3 and 4 induced the greatest cell cleavage arrest (0.5 micro g/ml of each compound resulted in >75% cleavage arrest), but cell cleavage inhibitory activity became weak when C-16 had an acyl residue. In contrast, the jatrophane diterpene kansuinin D (9) showed no activity.

Regio- and stereo-selective hydroxylations of ingenane diterpenoids by Mortierella ramanniana and Gibberella fujikuroi.[Reference: WebLink]

Chinese Journal of Natural Medicines, 2016 , 14 (12) :939-945.

The regio- and stereo-selective hydroxylations of two ingenane diterpenoids, 20-Deoxyingenol (1) and 13-oxyingenol dodecanoat (2), by the filamentous fungi Mortierella ramanniana and Gibberella fujikuroi were investigated in the present study.
METHODS AND RESULTS:
Four undescribed metabolites (3-6) of substrate 1 and two undescribed metabolites (7 and 8) of substrate 2 were isolated. All the metabolites were identified as hydroxylated ingenane derivatives by extensive NMR and HR-ESI-MS data analyses. All the biotransformed compounds and the substrates were evaluated for their cytotoxicities against three human cancer cell lines, including human colon cancer Caco-2, breast cancer MCF-7, and adriamycin (ADM)-resistant MCF-7/ADM cell lines. All ingenane alcohols (1, and 3-6) displayed no significant cytotoxic activities. The substrate 13-oxyingenol dodecanoat (2) showed moderate cytotoxicity with IC50 values being 35.59 ± 5.37 μmol·L-1 (Caco-2), 24.04 ± 4.70 μmol·L-1 (MCF-7), and 22.24 ± 5.19 μmol·L-1 (MCF-7/ADM). However, metabolites 7 and 8 displayed no significant cytotoxicity.
CONCLUSIONS:
These results indicated that the hydroxylation at the C-13 aliphatic acid ester of substrate 2 can significantly reduce the cytotoxic activity.

20-Deoxyingenol Dilution Calculator

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20-Deoxyingenol Molarity Calculator

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Preparing Stock Solutions of 20-Deoxyingenol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0084 mL 15.0421 mL 30.0842 mL 60.1685 mL 75.2106 mL
5 mM 0.6017 mL 3.0084 mL 6.0168 mL 12.0337 mL 15.0421 mL
10 mM 0.3008 mL 1.5042 mL 3.0084 mL 6.0168 mL 7.5211 mL
50 mM 0.0602 mL 0.3008 mL 0.6017 mL 1.2034 mL 1.5042 mL
100 mM 0.0301 mL 0.1504 mL 0.3008 mL 0.6017 mL 0.7521 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on 20-Deoxyingenol

20-Deoxyingenol is a natural compound.

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References on 20-Deoxyingenol

Diterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of Xenopus (part 2).[Pubmed:12913231]

Chem Pharm Bull (Tokyo). 2003 Aug;51(8):935-41.

Four new ingenane-type diterpenes, 3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-O-acetylingenol (1), 3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-Deoxyingenol (2), 3-O-(2E,4Z-decadienoyl)-20-Deoxyingenol (3), and 3-O-(2E,4E-decadienoyl)-20-Deoxyingenol (4), two new jatrophane-type diterpenes, kansuinins D (9) and E (10), and four known ingenane-type diterpenes were isolated from the root of Euphorbia kansui. Their structures were elucidated by spectroscopic and chemical analysis, and individual Xenopus cells at the blastular stage were cultured with the diterpenes to test for biological activity. 20-Deoxyingenol diterpenes 3 and 4 induced the greatest cell cleavage arrest (0.5 micro g/ml of each compound resulted in >75% cleavage arrest), but cell cleavage inhibitory activity became weak when C-16 had an acyl residue. In contrast, the jatrophane diterpene kansuinin D (9) showed no activity.

Description

20-Deoxyingenol is a natural compound.

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