MedKoo Cat#: 578675 | Name: Obtusaquinone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Obtusaquinone is a potent antineoplastic agent with promising in vivo activity in glioblastoma and breast cancer through the activation of oxidative stress. Obtusaquinone is able to penetrate the brain and functionally target brain tumors. Obtusaquinone showed improved pharmacological properties, including enhanced potency, stability, and solubility, retains the antineoplastic properties in a xenograft mouse model. Obtusaquinone significantly inhibited cell survival of patient-derived pHGG cells in culture. Obtusaquinone inhibited tumor growth and extended survival in 2 different orthotopic xenograft models. Mechanistically, OBT induced ER stress through abnormal ROS accumulation.

Chemical Structure

Obtusaquinone
Obtusaquinone
CAS#21105-15-7

Theoretical Analysis

MedKoo Cat#: 578675

Name: Obtusaquinone

CAS#: 21105-15-7

Chemical Formula: C16H14O3

Exact Mass: 254.0943

Molecular Weight: 254.28

Elemental Analysis: C, 75.58; H, 5.55; O, 18.88

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
62745-67-9 (alternate)
Synonym
Obtusaquinone
IUPAC/Chemical Name
2,5-Cyclohexadien-1-one, 2-hydroxy-5-methoxy-4-(3-phenyl-2-propenylidene)-, (E,E)-
InChi Key
LUZUAYAKZLCOCQ-GKPGWJKISA-N
InChi Code
InChI=1S/C16H14O3/c1-19-16-11-15(18)14(17)10-13(16)9-5-8-12-6-3-2-4-7-12/h2-11,17H,1H3/b8-5+,13-9-
SMILES Code
COC1=CC(=O)C(=C/C/1=C/C=C/c2ccccc2)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 254.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Teng J, Lashgari G, Tabet EI, Tannous BA. The natural compound obtusaquinone targets pediatric high-grade gliomas through ROS-mediated ER stress. Neurooncol Adv. 2020 Aug 27;2(1):vdaa106. doi: 10.1093/noajnl/vdaa106. PMID: 33134921; PMCID: PMC7592425. 2: Badr CE, da Hora CC, Kirov AB, Tabet E, Amante R, Maksoud S, Nibbs AE, Fitzsimons E, Boukhali M, Chen JW, Chiu NHL, Nakano I, Haas W, Mazitschek R, Tannous BA. Obtusaquinone: A Cysteine-Modifying Compound That Targets Keap1 for Degradation. ACS Chem Biol. 2020 Jun 19;15(6):1445-1454. doi: 10.1021/acschembio.0c00104. Epub 2020 May 8. PMID: 32338864; PMCID: PMC7995447. 3: Badr CE, Van Hoppe S, Dumbuya H, Tjon-Kon-Fat LA, Tannous BA. Targeting cancer cells with the natural compound obtusaquinone. J Natl Cancer Inst. 2013 May 1;105(9):643-53. doi: 10.1093/jnci/djt037. Epub 2013 Mar 11. PMID: 23479453; PMCID: PMC3691947. 4: Moratinos MM, Tevar E, Conde-Salazar L. Contact allergy to a cocobolo bracelet. Dermatitis. 2005 Sep;16(3):139-41. PMID: 16242087. 5: Barragán-Huerta BE, Peralta-Cruz J, González-Laredo RF, Karchesy J. Neocandenatone, an isoflavan-cinnamylphenol quinone methide pigment from Dalbergia congestiflora. Phytochemistry. 2004 Apr;65(7):925-8. doi: 10.1016/j.phytochem.2003.11.011. PMID: 15081296. 6: Guanche AD, Prawer S. Generalized eczematous contact dermatitis from cocobolo wood. Am J Contact Dermat. 2003 Jun;14(2):90-2. PMID: 14749027. 7: Hausen BM. Allergic contact dermatitis from a wooden necklace. Am J Contact Dermat. 1997 Sep;8(3):185-7. PMID: 9249295. 8: Rackett SC, Zug KA. Contact dermatitis to multiple exotic woods. Am J Contact Dermat. 1997 Jun;8(2):114-7. PMID: 9153334. 9: Hausen BM, Münster G. Cocobolo-Holz, ein vergessenes Ekzematogen? Neuere Erkenntnisse über das Hauptallergen des Cocobolo-Holzes (Dalbergia sp.) [Cocobolo wood, a forgotten eczematogen? Recent findings on the skin allergen of cocobolo wood (Dalbergia sp.)]. Derm Beruf Umwelt. 1983;31(4):110-7. German. PMID: 6226513.