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20-Deoxyingenol

Cat No.:V30201 Purity: ≥98%
20-Deoxyingenol is a diterpene extracted from the roots of Euphorbia kansui.
20-Deoxyingenol
20-Deoxyingenol Chemical Structure CAS No.: 54706-99-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes
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Product Description
20-Deoxyingenol is a diterpene extracted from the roots of Euphorbia kansui. 20-Deoxyingenol promotes autophagy and lysosomal biogenesis by promoting nuclear translocation of transcription factor EB (TFEB) in vitro. 20-Deoxyingenol may be utilized in osteoarthritis (OA) research.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
20-Deoxyingenol (2.5-10 mM; 24 hours) protects chondrocytes from cell death induced by tert-butyl hydroperoxide solution (TBHP; 100 μM) [2]. 20-Deoxyingenol (5-10 mM) can reduce the TBHP-induced upregulation of the apoptotic protein cleaved-caspase3 and the senescence protein p16INK4a in chondrocytes [2]. At concentrations below 10 mM, 20-Deoxyingenol (2.5–40 mM; 24 h) has no cytotoxic effect on chondrocytes [2]. In chondrocytes treated with TBHP, 20-Deoxyingenol (10 mM) restores autophagic flux over a 24-hour period [2]. 20-Deoxyingenol (4-10 mM; 24 hours) promotes nuclear levels of TFEB in TBHP-treated chondrocytes [2].
ln Vivo
In a mouse DMM model, 20-Deoxyingenol (20 mg/kg/d; intraperitoneal injection for 8 weeks) can slow the advancement of OA [2].
Animal Protocol
Animal/Disease Models: 10weeks old C57BL/6 male wild-type (WT) mice with unstable medial meniscus (DMM) [2]
Doses: 20 mg/kg
Route of Administration: intraperitoneal (ip) injection, one time/day, results for eight consecutive weeks
Experimental Results: Compared with the DMM group, the joint space was slightly wider and bone density and calcification were diminished. Inhibits the reduction of hyaline cartilage (HC) thickness and reduces the disorder and hypertrophy of chondrocytes in mouse joint tissue after DMM surgery. The surface of articular cartilage is less eroded and contains more proteoglycans. There are more positive staining spots for LAMP1 and LC3 II, and fewer positive staining spots for cleaved-caspase3 and P16INK4a. Increased nuclear levels of TFEB.
References

[1]. Isolation and structures of 20-deoxyingenol new diterpene, derivatives and ingenol derivative obtained from “kansui”. Tetrahedron Letters. 1974; 15(29): 2527-2528.

[2]. 20-Deoxyingenol alleviates osteoarthritis by activating TFEB in chondrocytes. Pharmacol Res. 2021 Jan 15;165:105361.

Additional Infomation
20-Deoxyingenol has been reported in Euphorbia peplus and Euphorbia segetalis with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H28O4
Molecular Weight
332.4
Exact Mass
332.198
CAS #
54706-99-9
PubChem CID
11290503
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
470.5±45.0 °C at 760 mmHg
Flash Point
252.4±25.2 °C
Vapour Pressure
0.0±2.6 mmHg at 25°C
Index of Refraction
1.605
LogP
3.51
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Heavy Atom Count
24
Complexity
690
Defined Atom Stereocenter Count
8
SMILES
C[C@@H]1C[C@@H]2[C@@H](C2(C)C)[C@@H]3C=C([C@H]([C@]4([C@@]1(C3=O)C=C([C@@H]4O)C)O)O)C
InChi Key
FOSYZKSOJUQLTD-NHPMXQBPSA-N
InChi Code
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
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
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~150.41 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (7.52 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (7.52 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.52 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0084 mL 15.0421 mL 30.0842 mL
5 mM 0.6017 mL 3.0084 mL 6.0168 mL
10 mM 0.3008 mL 1.5042 mL 3.0084 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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