A precursor of paclitaxel and an apoptotic agent
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Baccatin III

Item No. 21404

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one
CAS Number
27548-93-2
Synonyms
  • NSC 330753
Molecular Formula
C31H38O11
Formula Weight
586.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/ml
λmax
229 nm
SMILES
O[C@H]1C[C@@]([H])(OC2)[C@@]2([C@@]([H])([C@H](OC(C3=CC=CC=C3)=O)[C@@](C[C@@H](C(C)=C4[C@H]5OC(C)=O)O)(O)C4(C)C)[C@]1(C)C5=O)OC(C)=O
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
InChi Key
OVMSOCFBDVBLFW-VHLOTGQHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    Product Description

    Baccatin III is a polycyclic diterpene originally isolated from the yew tree (Taxus) that is a precursor of paclitaxel (Item No. 10461).1,2 Baccatin III induces apoptosis in JR4-Jurkat leukemia, HepG2 liver hepatocellular carcinoma, HeLa cervical, OVCAR-3 ovarian carcinoma, and T47D breast cancer cell lines (IC50s = 3.5, 3, 4, 5, and 2 μM, respectively).3 It dose-dependently increases the antigen presenting cell (APC) capacity of bone marrow-derived dendritic cells (BM-DCs) sensitized to OVA peptide but does not affect their phagocytic activity.4 Baccatin III (0.5 mg/kg per day) decreases tumor growth of 4T1 mammary carcinoma and CT26 colon carcinoma flank implants by 65.6 and 63.9%, respectively, as well as inhibits the accumulation and activity of myeloid-derived suppressor cells (MDSCs) in spleen in immunocompetent mice.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chan, K.C., Alvarado, A.B., McGuire, M.T., et al. High-performance liquid chromatography and micellar electrokinetic chromatography of taxol and related taxanes from bark and needle extracts of Taxus species. J. Chromatogr. B Biomed. Appl 657(2), 301-306 (1994).

    2. Kingston, D.G.I. Recent advances in the chemistry of taxol. J. Nat. Prod. 63(5), 726-734 (2000).

    3. Chakravarthi, B.V., Sujay, R., Kuriakose, G.C., et al. Inhibition of cancer cell proliferation and apoptosis-inducing activity of fungal taxol and its precursor baccatin III purified from endophytic Fusarium solani. Cancer Cell Int. 13(1), (2013).

    4. Lee, Y.-H., Lee, Y.-R., Kim, K.-H., et al. Baccatin III, a synthetic precursor of taxol, enhances MHC-restricted antigen presentation in dendritic cells. Int. Immunopharmacol. 11(8), 982-991 (2011).

    5. Lee, Y.-H., Lee, Y.-R., Park, C.-S., et al. 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. 21(2), 487-493 (2014).