yingweiwo

14-Deoxyandrographolide

Cat No.:V30570 Purity: ≥98%
14-Deoxyandrographolide is a labdanum diterpene with calcium channel blocking activity.
14-Deoxyandrographolide
14-Deoxyandrographolide Chemical Structure CAS No.: 4176-97-0
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
100mg
Other Sizes
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text

 

  • Business Relationship with 5000+ Clients Globally
  • Major Universities, Research Institutions, Biotech & Pharma
  • Citations by Top Journals: Nature, Cell, Science, etc.
Top Publications Citing lnvivochem Products
Product Description
14-Deoxyandrographolide is a labdanum diterpene with calcium channel blocking activity. 14-Deoxyandrographolide gradually desensitizes hepatocytes to TNF-α-mediated apoptosis by inducing the release of TNFRSF1A.
Biological Activity I Assay Protocols (From Reference)
Targets
- 14-Deoxyandrographolide targets calcium-mediated signaling pathways in rat uterine smooth muscle.[1]
- 14-Deoxyandrographolide targets tumor necrosis factor receptor superfamily member 1A (TNFR1A) in hepatocytes, acting via the NO/cGMP pathway [2]
ln Vitro
- Inhibition of rat uterine smooth muscle contractility: Isolated rat uterine smooth muscle strips were treated with 14-Deoxyandrographolide at 10, 30, and 100 μM. At 100 μM, it inhibited KCl (60 mM)-induced contractions by 62% and oxytocin (10 nM)-induced contractions by 58%, compared to the control group. The inhibition was concentration-dependent, with no significant effect at 10 μM. Mechanistically, it reduced calcium influx into smooth muscle cells, as evidenced by decreased intracellular calcium levels (measured via fluorescent calcium indicator)[1]
- Desensitization of hepatocytes to TNF-α-induced apoptosis: Primary rat hepatocytes were pretreated with 14-Deoxyandrographolide (10, 30 μM) for 1 hour, then exposed to TNF-α (10 ng/mL) for 24 hours. The 30 μM dose reduced apoptosis rate by 45% (assessed via Hoechst 33258 staining) compared to the TNF-α-only group. It also increased the release of TNFR1A into the culture supernatant by 35% (30 μM) and elevated intracellular NO levels by 40% (30 μM) and cGMP levels by 38% (30 μM). The effect was reversed by a NO synthase inhibitor (L-NAME), confirming dependence on the NO/cGMP pathway[2]
Enzyme Assay
- NO concentration assay in hepatocytes: Primary rat hepatocytes were incubated with 14-Deoxyandrographolide (10, 30 μM) for 1 hour. The culture supernatant was collected, and NO concentration was measured using the nitrate reductase method: supernatant was mixed with nitrate reductase and cofactors, incubated at 37°C for 30 minutes, then reacted with Griess reagent. Absorbance was read at 540 nm, and NO concentration was calculated from a standard curve[2]
Cell Assay
- Hepatocyte apoptosis assay: Primary rat hepatocytes were seeded in 6-well plates at 5×10⁵ cells/well and cultured for 24 hours. Cells were pretreated with 14-Deoxyandrographolide (10, 30 μM) for 1 hour, then treated with TNF-α (10 ng/mL) for 24 hours. Apoptosis was detected by two methods: 1) Hoechst 33258 staining (counting apoptotic nuclei under fluorescence microscope, apoptosis rate = apoptotic nuclei/total nuclei × 100%); 2) caspase-3 activity assay (lysing cells, incubating with caspase-3 substrate, measuring fluorescence at 460 nm after excitation at 380 nm). The 30 μM dose reduced caspase-3 activity by 42% compared to the TNF-α-only group[2]
Animal Protocol
- Rat uterine smooth muscle preparation: Female Sprague-Dawley rats (200–220 g) in estrus were sacrificed by cervical dislocation. The uterus was excised, cleaned of connective tissue, and cut into 2–3 mm longitudinal strips. Each strip was mounted in a 5 mL organ bath containing Krebs-Ringer bicarbonate solution (maintained at 37°C, gassed with 95% O₂ and 5% CO₂) and connected to a force transducer to record contractile tension. After a 30-minute equilibration period, KCl (60 mM) or oxytocin (10 nM) was added to induce contractions. Once contractions stabilized, 14-Deoxyandrographolide (dissolved in DMSO, diluted in Krebs solution to final concentrations of 10, 30, 100 μM) was added sequentially, and contractile changes were recorded for 20 minutes per concentration[1]
References

[1]. Effect of 14-deoxyandrographolide on calcium-mediated rat uterine smooth muscle contractility. Phytother Res. 2003;17(9):1011-1015.

[2]. 14-Deoxyandrographolide desensitizes hepatocytes to tumour necrosis factor-alpha-induced apoptosis through calcium-dependent tumour necrosis factor receptor superfamily member 1A release via the NO/cGMP pathway. Br J Pharmacol. 2010 Aug;160.

Additional Infomation
14-Deoxyandrographolide is a diterpenoid lactone.
It has been reported that 14-deoxyandrographolide exists in Andrographis paniculata and Antrodia camphoratus, and there are related data reports.
- The inhibitory effect of 14-deoxyandrographolide on uterine smooth muscle contraction is mediated by reducing the influx of extracellular calcium ions, rather than blocking the release of intracellular calcium ions[1].
- 14-deoxyandrographolide desensitizes hepatocytes to TNF-α-induced apoptosis by promoting the release of TNFR1A (reducing the amount of TNFR1A that can bind to TNF-α on the cell surface), and this process requires activation of the NO/cGMP pathway[2].
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H30O4
Molecular Weight
334.4498
Exact Mass
334.214
CAS #
4176-97-0
PubChem CID
11624161
Appearance
White to off-white solid powder
Density
1.15g/cm3
Boiling Point
509.5ºC at 760 mmHg
Melting Point
176-178ºC
Flash Point
177.3ºC
Index of Refraction
1.551
LogP
2.991
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
24
Complexity
566
Defined Atom Stereocenter Count
5
SMILES
C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2CCC3=CCOC3=O)(C)CO)O
InChi Key
GVRNTWSGBWPJGS-YSDSKTICSA-N
InChi Code
InChI=1S/C20H30O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h9,15-17,21-22H,1,4-8,10-12H2,2-3H3/t15-,16+,17-,19+,20+/m1/s1
Chemical Name
4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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 : ~100 mg/mL (~299.00 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.47 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 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.

Solubility in Formulation 2: ≥ 2.5 mg/mL (7.47 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 2.9900 mL 14.9499 mL 29.8998 mL
5 mM 0.5980 mL 2.9900 mL 5.9800 mL
10 mM 0.2990 mL 1.4950 mL 2.9900 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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.)
+
+
+

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.

Contact Us