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MedKoo Cat#: 146200 | Name: Sorbicillin

Description:

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

Sorbicillin is a polyketide-derived secondary metabolite produced by certain fungi, notably species of Penicillium and Trichoderma. It exhibits a range of bioactivities, including antibacterial, antifungal, and cytotoxic effects, making it a candidate for pharmaceutical and agricultural applications. Sorbicillin and its derivatives act by disrupting microbial cell membranes and interfering with essential metabolic processes. Ongoing research is investigating its potential as a lead compound for novel antimicrobial and anticancer therapies.

Chemical Structure

Sorbicillin
Sorbicillin
CAS#79950-85-9

Theoretical Analysis

MedKoo Cat#: 146200

Name: Sorbicillin

CAS#: 79950-85-9

Chemical Formula: C14H16O3

Exact Mass: 232.1099

Molecular Weight: 232.28

Elemental Analysis: C, 72.39; H, 6.94; O, 20.66

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
Sorbicillin;
IUPAC/Chemical Name
(2E,4E)-1-(2,4-dihydroxy-3,5-dimethylphenyl)hexa-2,4-dien-1-one
InChi Key
RKKPUBAAIGFXOG-YTXTXJHMSA-N
InChi Code
1S/C14H16O3/c1-4-5-6-7-12(15)11-8-9(2)13(16)10(3)14(11)17/h4-8,16-17H,1-3H3/b5-4+,7-6+
SMILES Code
C\C=C\C=C\C(=O)C1=CC(C)=C(O)C(C)=C1O
Appearance
To be determined
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 232.28 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: Maskey RP, Grün-Wollny I, Laatsch H. Sorbicillin analogues and related dimeric compounds from Penicillium notatum. J Nat Prod. 2005 Jun;68(6):865-70. doi: 10.1021/np040137t. PMID: 15974609. 2: Jiang CS, Zhou ZF, Yang XH, Lan LF, Gu YC, Ye BP, Guo YW. Antibacterial sorbicillin and diketopiperazines from the endogenous fungus Penicillium sp. GD6 associated Chinese mangrove Bruguiera gymnorrhiza. Chin J Nat Med. 2018 May;16(5):358-365. doi: 10.1016/S1875-5364(18)30068-2. PMID: 29860997. 3: Yao Y, Li J, Jiang CS, Zhao XX, Miao ZH, Liu HT, Zheng P, Ya WX, Li WQ. Trichodimerol and sorbicillin induced apoptosis of HL-60 cells is mediated by reactive oxygen species. Pharmazie. 2015 Jun;70(6):394-8. PMID: 26189301. 4: Guzmán-Chávez F, Salo O, Nygård Y, Lankhorst PP, Bovenberg RAL, Driessen AJM. Mechanism and regulation of sorbicillin biosynthesis by Penicillium chrysogenum. Microb Biotechnol. 2017 Jul;10(4):958-968. doi: 10.1111/1751-7915.12736. Epub 2017 Jun 15. PMID: 28618182; PMCID: PMC5481523. 5: Kaya Tilki E, Engür Öztürk S, Özarda MG, Cantürk Z, Dikmen M. Investigation of the neuroprotective and neuritogenic effects of halotolerant Penicillium flavigenum-derived sorbicillin-like compounds on PC-12 Adh cells. Cytotechnology. 2021 Dec;73(6):801-813. doi: 10.1007/s10616-021-00498-9. Epub 2021 Oct 4. PMID: 34776630; PMCID: PMC8554936. 6: Ma L, Liu W, Huang Y, Rong X. Two acid sorbicillin analogues from saline lands-derived fungus Trichoderma sp. J Antibiot (Tokyo). 2011 Sep;64(9):645-7. doi: 10.1038/ja.2011.54. Epub 2011 Jul 20. PMID: 21772303. 7: Reátegui RF, Wicklow DT, Gloer JB. Phaeofurans and sorbicillin analogues from a fungicolous Phaeoacremonium species (NRRL 32148). J Nat Prod. 2006 Jan;69(1):113-7. doi: 10.1021/np0504199. PMID: 16441079; PMCID: PMC2533440. 8: Pettus LH, Van De Water RW, Pettus TR. Synthesis of (+/-)-epoxysorbicillinol using a novel cyclohexa-2,5-dienone with synthetic applications to other sorbicillin derivatives. Org Lett. 2001 Mar 22;3(6):905-8. doi: 10.1021/ol0155438. PMID: 11263912; PMCID: PMC1360178. 9: Abe N, Murata T, Hirota A. Novel Oxidized Sorbicillin Dimers with 1,1-Diphenyl-2-picrylhydrazyl-Radical Scavenging Activity from a Fungus. Biosci Biotechnol Biochem. 1998;62(11):2120-6. doi: 10.1271/bbb.62.2120. PMID: 27393585. 10: Chakrabarty S, Romero EO, Pyser JB, Yazarians JA, Narayan ARH. Chemoenzymatic Total Synthesis of Natural Products. Acc Chem Res. 2021 Mar 16;54(6):1374-1384. doi: 10.1021/acs.accounts.0c00810. Epub 2021 Feb 18. PMID: 33600149; PMCID: PMC8210581. 11: Lan WJ, Zhao Y, Xie ZL, Liang LZ, Shao WY, Zhu LP, Yang DP, Zhu XF, Li HJ. Novel sorbicillin analogues from the marine fungus Trichoderma sp. associated with the seastar Acanthaster planci. Nat Prod Commun. 2012 Oct;7(10):1337-40. PMID: 23157004. 12: Salo O, Guzmán-Chávez F, Ries MI, Lankhorst PP, Bovenberg RAL, Vreeken RJ, Driessen AJM. Identification of a Polyketide Synthase Involved in Sorbicillin Biosynthesis by Penicillium chrysogenum. Appl Environ Microbiol. 2016 Jun 13;82(13):3971-3978. doi: 10.1128/AEM.00350-16. PMID: 27107123; PMCID: PMC4907180. 13: Meng J, Wang X, Xu D, Fu X, Zhang X, Lai D, Zhou L, Zhang G. Sorbicillinoids from Fungi and Their Bioactivities. Molecules. 2016 Jun 1;21(6):715. doi: 10.3390/molecules21060715. PMID: 27258245; PMCID: PMC6273499. 14: Abdel-Lateff A. Bioproduction of sorbicillin derivatives from marine Trichoderma sp. Z Naturforsch C J Biosci. 2008 Sep-Oct;63(9-10):631-5. doi: 10.1515/znc-2008-9-1002. PMID: 19040097. 15: Milzarek TM, Gulder TAM. Chemo-enzymatic total synthesis of the spirosorbicillinols. Commun Chem. 2023 Sep 6;6(1):187. doi: 10.1038/s42004-023-00996-1. PMID: 37674031; PMCID: PMC10482909. 16: CRAM DJ. Mold metabolites; the structure of sorbicillin, a pigment produced by the mold Penicillium notatum. J Am Chem Soc. 1948 Dec;70(12):4240-3. doi: 10.1021/ja01192a077. PMID: 18105979. 17: Kahlert L, Bassiony EF, Cox RJ, Skellam EJ. Diels-Alder Reactions During the Biosynthesis of Sorbicillinoids. Angew Chem Int Ed Engl. 2020 Mar 27;59(14):5816-5822. doi: 10.1002/anie.201915486. Epub 2020 Feb 4. PMID: 31943627; PMCID: PMC7154774. 18: Abe N, Arakawa T, Yamamoto K, Hirota A. Biosynthesis of bisorbicillinoid in Trichoderma sp. USF-2690; evidence for the biosynthetic pathway, via sorbicillinol, of sorbicillin, bisorbicillinol, bisorbibutenolide, and bisorbicillinolide. Biosci Biotechnol Biochem. 2002 Oct;66(10):2090-9. doi: 10.1271/bbb.66.2090. PMID: 12450119. 19: Derntl C, Guzmán-Chávez F, Mello-de-Sousa TM, Busse HJ, Driessen AJM, Mach RL, Mach-Aigner AR. In Vivo Study of the Sorbicillinoid Gene Cluster in Trichoderma reesei. Front Microbiol. 2017 Oct 20;8:2037. doi: 10.3389/fmicb.2017.02037. PMID: 29104566; PMCID: PMC5654950. 20: Milzarek TM, Gulder TAM. The fungal natural product class of the sorbicillinoids: structures, bioactivities, biosynthesis, and synthesis. Nat Prod Rep. 2025 Mar 19;42(3):482-500. doi: 10.1039/d4np00059e. PMID: 39868484.