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Baccatin III

Cat No.:V31108 Purity: ≥98%
Baccatin III is a naturally occurring compound extracted from the Pacific yew tree and its relatives.
Baccatin III
Baccatin III Chemical Structure CAS No.: 27548-93-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Baccatin III is a naturally occurring compound extracted from the Pacific yew tree and its relatives. Baccatin III can delay tumor development by reducing the accumulation of MDSCs and inhibiting their function.
Biological Activity I Assay Protocols (From Reference)
Targets
- Myeloid-derived suppressor cells (MDSCs) accumulation and immunosuppressive activity-related targets [1]
ln Vitro
- Baccatin III inhibited the immunosuppressive activity of MDSCs in vitro. At concentrations of 5, 10, and 20 μM, it reversed MDSC-mediated suppression of T cell proliferation by 32±3%, 58±4%, and 75±5%, respectively [1]
- It did not affect the viability of MDSCs or T cells at concentrations up to 20 μM, with cell viability maintained above 90% [1]
- It downregulated the expression of immunosuppressive molecules (arginase-1, iNOS) in MDSCs: 20 μM reduced arginase-1 activity by 62±4% and iNOS mRNA levels by 57±3% [1]
ln Vivo
- In C57BL/6 mice bearing LLC Lewis lung carcinoma: Intraperitoneal injection of Baccatin III (5, 10 mg/kg, every other day for 14 days) dose-dependently reduced MDSC accumulation. The percentage of Gr-1⁺CD11b⁺ MDSCs in the spleen decreased by 35±3% (5 mg/kg) and 52±4% (10 mg/kg), and in tumor tissues by 42±3% (5 mg/kg) and 61±5% (10 mg/kg) [1]
- It enhanced antitumor immunity: 10 mg/kg Baccatin III increased CD4⁺ and CD8⁺ T cell proliferation in tumor-draining lymph nodes by 48±4% and 55±5%, respectively, and elevated IFN-γ production by T cells by 63±4% [1]
- It inhibited tumor growth: 10 mg/kg dose reduced tumor volume by 58±4% and tumor weight by 62±3% compared to the control group [1]
- Similar effects were observed in B16-F10 melanoma-bearing mice: 10 mg/kg Baccatin III reduced splenic MDSCs by 49±4% and tumor growth by 55±3% [1]
Cell Assay
- MDSC isolation and culture assay: MDSCs were isolated from the spleen of LLC tumor-bearing mice by magnetic bead sorting (Gr-1⁺CD11b⁺ selection). Isolated MDSCs were incubated with Baccatin III (5, 10, 20 μM) for 24 hours, then co-cultured with CFSE-labeled splenic T cells (from naive mice) for 72 hours. T cell proliferation was analyzed by flow cytometry [1]
- Immunosuppressive molecule detection assay: MDSCs treated with Baccatin III (10, 20 μM) for 24 hours were lysed. Arginase-1 activity was measured by colorimetric assay; iNOS mRNA levels were detected by RT-PCR [1]
- Cell viability assay: MDSCs and T cells were treated with Baccatin III (5–20 μM) for 24 hours, and viability was measured by MTT assay [1]
Animal Protocol
- LLC Lewis lung carcinoma model: C57BL/6 mice (6–8 weeks old) were subcutaneously injected with LLC cells (5×10⁶ cells/mouse) into the right flank. When tumors reached 50–100 mm³, mice were randomly divided into control (vehicle) and Baccatin III groups (5, 10 mg/kg, intraperitoneal injection every other day for 14 days). Tumor volume was measured every 3 days; mice were sacrificed, and spleen/tumor tissues were collected for flow cytometry (MDSC percentage) and T cell function analysis [1]
- B16-F10 melanoma model: Mice were subcutaneously injected with B16-F10 cells (2×10⁶ cells/mouse). Baccatin III (10 mg/kg) was administered as above. Tumor growth and MDSC accumulation were evaluated similarly [1]
- Baccatin III was dissolved in DMSO (final concentration ≤5%) and diluted with normal saline before injection [1]
Toxicity/Toxicokinetics
No significant systemic toxicity was observed: Mice treated with baccatin III (at doses up to 10 mg/kg) did not show significant weight loss, and no abnormal damage was found in liver and kidney histology [1]
- At therapeutic concentrations, baccatin III did not produce cytotoxicity against normal immune cells (T cells, B cells) [1]
References

[1]. Baccatin III, a precursor for the semisynthesis of paclitaxel, inhibits the accumulation and suppressive activity of myeloid-derived suppressor cells in tumor-bearing mice. Int Immunopharmacol. 2014 Aug;21(2):487-93.

Additional Infomation
Baccatin III is a tetracyclic diterpenoid compound isolated from plants of the genus Taxus. It is a plant metabolite. It is a tetracyclic diterpenoid compound with structures of acetate and benzoate. It is derived from the hydride of taxane. Baccatin III has been reported to exist in Taxus sumatrana, Taxus cuspidata, and other organisms with relevant data. Baccatin III is a compound extracted from the needles of Taxus baccata and used as a precursor to paclitaxel.
- Baccatin III is a natural diterpenoid compound isolated from the genus Taxus and is a key precursor for the semi-synthesis of paclitaxel[1]
- Its antitumor mechanism involves targeting myeloid-derived suppressor cells (MDSCs) to reduce their accumulation and immunosuppressive activity, thereby restoring antitumor T cell responses[1]
- Unlike paclitaxel, it exerts its antitumor effect primarily through immunomodulation rather than direct cytotoxicity on tumor cells[1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C31H38O11
Molecular Weight
586.6268
Exact Mass
586.241
CAS #
27548-93-2
PubChem CID
65366
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
713.6±60.0 °C at 760 mmHg
Melting Point
229-234 °C
Flash Point
226.9±26.4 °C
Vapour Pressure
0.0±2.4 mmHg at 25°C
Index of Refraction
1.605
LogP
4.06
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
7
Heavy Atom Count
42
Complexity
1200
Defined Atom Stereocenter Count
9
SMILES
CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)OC(=O)C
InChi Key
OVMSOCFBDVBLFW-VHLOTGQHSA-N
InChi Code
InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24-,26-,29+,30-,31+/m0/s1
Chemical Name
[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
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 : ~33.33 mg/mL (~56.82 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.55 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 20.8 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: ≥ 2.08 mg/mL (3.55 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 20.8 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: ≥ 2.08 mg/mL (3.55 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 20.8 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 1.7047 mL 8.5233 mL 17.0465 mL
5 mM 0.3409 mL 1.7047 mL 3.4093 mL
10 mM 0.1705 mL 0.8523 mL 1.7047 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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