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MedKoo Cat#: 585210 | Name: Squamocin

Description:

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

Squamocin, also known as Annonin I, is a trihydroxy-bis-tetrahydrofuran fatty acid γ-lactone (acetogenin) isolated from Annona squamosa L.(Annonaceae) with larvicidal and cytotoxic properties.

Chemical Structure

Squamocin
Squamocin
CAS#120298-30-8

Theoretical Analysis

MedKoo Cat#: 585210

Name: Squamocin

CAS#: 120298-30-8

Chemical Formula: C39H70O5

Exact Mass: 618.5223

Molecular Weight: 618.98

Elemental Analysis: C, 75.68; H, 11.40; O, 12.92

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 #
No Data
Synonym
Squamocin; Annonin I;
IUPAC/Chemical Name
2(5H)-Furanone, 3-(13-(5'-(1,5-dimethylundecyl)octahydro(2,2'-bifuran)-5-yl)-13-hydroxytridecyl)-5-methyl-
InChi Key
YDALDJGZOJJJLD-UHFFFAOYSA-N
InChi Code
InChI=1S/C39H70O5/c1-5-6-7-16-20-30(2)21-19-22-31(3)35-25-27-37(43-35)38-28-26-36(44-38)34(40)24-18-15-13-11-9-8-10-12-14-17-23-33-29-32(4)42-39(33)41/h29-32,34-38,40H,5-28H2,1-4H3
SMILES Code
O=C1OC(C)C=C1CCCCCCCCCCCCC(C2CCC(C3OC(C(C)CCCC(C)CCCCCC)CC3)O2)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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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 618.98 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: Costa MS, Cossolin JF, Pereira MJ, Sant'Ana AE, Lima MD, Zanuncio JC, Serrão JE. Larvicidal and cytotoxic potential of squamocin on the midgut of Aedes aegypti (Diptera: Culicidae). Toxins (Basel). 2014 Mar 26;6(4):1169-76. doi: 10.3390/toxins6041169. PubMed PMID: 24674934; PubMed Central PMCID: PMC4014726. 2: Wu SN, Chiang HT, Chang FR, Liaw CC, Wu YC. Stimulatory effects of squamocin, an Annonaceous acetogenin, on Ca(2+)-activated K+ current in cultured smooth muscle cells of human coronary artery. Chem Res Toxicol. 2003 Jan;16(1):15-22. PubMed PMID: 12693026. 3: Lee CC, Lin YH, Chang WH, Lin PC, Wu YC, Chang JG. Squamocin modulates histone H3 phosphorylation levels and induces G1 phase arrest and apoptosis in cancer cells. BMC Cancer. 2011 Feb 8;11:58. doi: 10.1186/1471-2407-11-58. PubMed PMID: 21299907; PubMed Central PMCID: PMC3055232. 4: Raynaud S, Fourneau C, Laurens A, Hocquemiller R, Loiseau P, Bories C. Squamocin and benzyl benzoate, acaricidal components of Uvaria pauci-ovulata bark extracts. Planta Med. 2000 Mar;66(2):173-5. PubMed PMID: 10763595. 5: da Silva Costa M, de Paula SO, Martins GF, Zanuncio JC, Santana AE, Serrão JE. Multiple Modes of Action of the Squamocin in the Midgut Cells of Aedes aegypti Larvae. PLoS One. 2016 Aug 17;11(8):e0160928. doi: 10.1371/journal.pone.0160928. eCollection 2016. PubMed PMID: 27532504; PubMed Central PMCID: PMC4988707. 6: Lu MC, Yang SH, Hwang SL, Lu YJ, Lin YH, Wang SR, Wu YC, Lin SR. Induction of G2/M phase arrest by squamocin in chronic myeloid leukemia (K562) cells. Life Sci. 2006 Apr 11;78(20):2378-83. Epub 2005 Nov 28. PubMed PMID: 16310807. 7: Yuan SS, Chang HL, Chen HW, Kuo FC, Liaw CC, Su JH, Wu YC. Selective cytotoxicity of squamocin on T24 bladder cancer cells at the S-phase via a Bax-, Bad-, and caspase-3-related pathways. Life Sci. 2006 Jan 18;78(8):869-74. Epub 2005 Sep 8. PubMed PMID: 16154156. 8: Shi JF, Wu P, Jiang ZH, Wei XY. Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins. Eur J Med Chem. 2014 Jan;71:219-28. doi: 10.1016/j.ejmech.2013.11.012. Epub 2013 Nov 15. PubMed PMID: 24308999. 9: Fiaz M, Martínez LC, Costa MDS, Cossolin JFS, Plata-Rueda A, Gonçalves WG, Sant'Ana AEG, Zanuncio JC, Serrão JE. Squamocin induce histological and ultrastructural changes in the midgut cells of Anticarsia gemmatalis (Lepidoptera: Noctuidae). Ecotoxicol Environ Saf. 2018 Jul 30;156:1-8. doi: 10.1016/j.ecoenv.2018.02.080. Epub 2018 Mar 7. PubMed PMID: 29524778. 10: Mangal M, Khan MI, Agarwal SM. Acetogenins as Potential Anticancer Agents. Anticancer Agents Med Chem. 2015;16(2):138-59. Review. PubMed PMID: 26118710. 11: Araya H, Sahai M, Singh S, Singh AK, Yoshida M, Hara N, Fujimoto Y. Squamocin-O(1) and squamocin-O(2), new adjacent bis-tetrahydrofuran acetogenins from the seeds of Annona squamosa. Phytochemistry. 2002 Dec;61(8):999-1004. PubMed PMID: 12453534. 12: Duval RA, Lewin G, Peris E, Chahboune N, Garofano A, Dröse S, Cortes D, Brandt U, Hocquemiller R. Heterocyclic analogues of squamocin as inhibitors of mitochondrial complex I. On the role of the terminal lactone of annonaceous acetogenins. Biochemistry. 2006 Feb 28;45(8):2721-8. PubMed PMID: 16489765. 13: Born L, Lieb F, Lorentzen JP, Moeschler H, Nonfon M, Söllner R, Wendisch D. [The Relative Configuration of Acetogenins Isolated from Annona squamosa: Annonin I (Squamocin) and Annonin VI]. Planta Med. 1990 Jun;56(3):312-6. German. PubMed PMID: 17221427. 14: Duval R, Lewin G, Hocquemiller R. Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction. Bioorg Med Chem. 2003 Aug 5;11(16):3439-46. PubMed PMID: 12878138. 15: Zhu XF, Liu ZC, Xie BF, Li ZM, Feng GK, Xie HH, Wu SJ, Yang RZ, Wei XY, Zeng YX. Involvement of caspase-3 activation in squamocin-induced apoptosis in leukemia cell line HL-60. Life Sci. 2002 Feb 1;70(11):1259-69. PubMed PMID: 11883704. 16: Parellada EA, Igarza M, Isacc P, Bardón A, Ferrero M, Ameta KL, Neske A. Squamocin, an annonaceous acetogenin, enhances naphthalene degradation mediated by Bacillus atrophaeus CN4. Rev Argent Microbiol. 2017 Jul - Sep;49(3):282-288. doi: 10.1016/j.ram.2017.03.004. Epub 2017 May 26. PubMed PMID: 28554707. 17: Levine RA, Richards KM, Tran K, Luo R, Thomas AL, Smith RE. Determination of Neurotoxic Acetogenins in Pawpaw (Asimina triloba) Fruit by LC-HRMS. J Agric Food Chem. 2015 Feb 4;63(4):1053-1056. doi: 10.1021/jf504500g. Epub 2015 Jan 22. PubMed PMID: 25594104. 18: Tam VT, Hieu BC, Chappe B. Squamocin and Rolliniastatin I from the Seeds of Annona reticulata. Planta Med. 1993 Dec;59(6):576. PubMed PMID: 17230372. 19: Derbré S, Gil S, Taverna M, Boursier C, Nicolas V, Demey-Thomas E, Vinh J, Susin SA, Hocquemiller R, Poupon E. Highly cytotoxic and neurotoxic acetogenins of the Annonaceae: new putative biological targets of squamocin detected by activity-based protein profiling. Bioorg Med Chem Lett. 2008 Nov 1;18(21):5741-4. doi: 10.1016/j.bmcl.2008.09.091. Epub 2008 Sep 30. PubMed PMID: 18851912. 20: Costa MS, Santana AE, Oliveira LL, Zanuncio JC, Serrão JE. Toxicity of squamocin on Aedes aegypti larvae, its predators and human cells. Pest Manag Sci. 2017 Mar;73(3):636-640. doi: 10.1002/ps.4350. Epub 2016 Aug 4. PubMed PMID: 27366879.