Austinol | CAS#72040-27-8 | biochemical

MedKoo Cat#: 146121 | Name: Austinol

Description:

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

Austinol is a natural compound derived from the Pseudomonas species, known for its antimicrobial and antifungal properties. It has been studied for its potential to treat infections caused by resistant microbial strains, especially in agricultural and clinical settings. Austinol exerts its effects by disrupting the integrity of microbial cell membranes and interfering with the synthesis of essential cellular components, leading to cell death.

Chemical Structure

Austinol

CAS#72040-27-8

Theoretical Analysis

MedKoo Cat#: 146121

Name: Austinol

CAS#: 72040-27-8

Chemical Formula: C25H30O8

Exact Mass: 458.1941

Molecular Weight: 458.51

Elemental Analysis: C, 65.49; H, 6.60; O, 27.91

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Austinol; Desacetylaustin;

IUPAC/Chemical Name

(3R,3'R,3a'R,6'S,7'S,11a'S,11b'R)-3a',7'-dihydroxy-2,2,3',6',8',11a'-hexamethyl-12'-methylene-3',3a',6',7',11',11a'-hexahydro-1'H,2H,4'H,6H,10'H-spiro[pyran-3,9'-[6,11b]methanobenzo[e]furo[3,4-c]oxocine]-1',4',6-trione

InChi Key

DNKFADXVMUNRRM-XOPCMRBUSA-N

InChi Code

1S/C25H30O8/c1-12-16-17(27)22(7)13(2)24(18(28)31-14(3)25(24,30)19(29)33-22)21(16,6)10-11-23(12)9-8-15(26)32-20(23,4)5/h8-9,14,17,27,30H,2,10-11H2,1,3-7H3/t14-,17+,21+,22+,23+,24+,25-/m1/s1

SMILES Code

C[C@H]1OC(=O)[C@]23C(=C)[C@](C)(OC(=O)[C@]12O)[C@@H](O)C4=C(C)[C@@]5(CC[C@]34C)C=CC(=O)OC5(C)C

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 458.51 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.

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: Matsuda Y, Awakawa T, Wakimoto T, Abe I. Spiro-ring formation is catalyzed by a multifunctional dioxygenase in austinol biosynthesis. J Am Chem Soc. 2013 Jul 31;135(30):10962-5. doi: 10.1021/ja405518u. Epub 2013 Jul 22. PMID: 23865690. 2: Lo HC, Entwistle R, Guo CJ, Ahuja M, Szewczyk E, Hung JH, Chiang YM, Oakley BR, Wang CC. Two separate gene clusters encode the biosynthetic pathway for the meroterpenoids austinol and dehydroaustinol in Aspergillus nidulans. J Am Chem Soc. 2012 Mar 14;134(10):4709-20. doi: 10.1021/ja209809t. Epub 2012 Feb 29. PMID: 22329759; PMCID: PMC3350773. 3: Park SC, Steffan BN, Yun Lim F, Gupta R, Ayaloglu Butun F, Chen H, Ye R, Decker T, Wu CC, Kelleher NL, Woo Bok J, Keller NP. Terpenoid balance in Aspergillus nidulans unveiled by heterologous squalene synthase expression. Sci Adv. 2024 Feb 23;10(8):eadk7416. doi: 10.1126/sciadv.adk7416. Epub 2024 Feb 21. PMID: 38381828; PMCID: PMC10881027. 4: Park SC, Steffan BN, Lim FY, Gupta R, Butun FA, Chen H, Ye R, Decker T, Wu CC, Kelleher NL, Bok JW, Keller NP. Terpenoid balance in Aspergillus nidulans unveiled by heterologous squalene synthase expression. bioRxiv [Preprint]. 2023 Oct 20:2023.10.20.563295. doi: 10.1101/2023.10.20.563295. Update in: Sci Adv. 2024 Feb 23;10(8):eadk7416. doi: 10.1126/sciadv.adk7416. PMID: 37905136; PMCID: PMC10614972. 5: Nakashima Y, Mori T, Nakamura H, Awakawa T, Hoshino S, Senda M, Senda T, Abe I. Structure function and engineering of multifunctional non-heme iron dependent oxygenases in fungal meroterpenoid biosynthesis. Nat Commun. 2018 Jan 9;9(1):104. doi: 10.1038/s41467-017-02371-w. PMID: 29317628; PMCID: PMC5760668. 6: Mo S, Yin J, Ye Z, Li F, Lin S, Zhang S, Yang B, Yao J, Wang J, Hu Z, Zhang Y. Asperanstinoids A-E: Undescribed 3,5-dimethylorsellinic acid-based meroterpenoids from Aspergillus calidoustus. Phytochemistry. 2021 Oct;190:112892. doi: 10.1016/j.phytochem.2021.112892. Epub 2021 Jul 31. PMID: 34343886. 7: Long Y, Cui H, Liu X, Xiao Z, Wen S, She Z, Huang X. Acetylcholinesterase Inhibitory Meroterpenoid from a Mangrove Endophytic Fungus Aspergillus sp. 16-5c. Molecules. 2017 May 3;22(5):727. doi: 10.3390/molecules22050727. PMID: 28467349; PMCID: PMC6154586. 8: Valiante V, Mattern DJ, Schüffler A, Horn F, Walther G, Scherlach K, Petzke L, Dickhaut J, Guthke R, Hertweck C, Nett M, Thines E, Brakhage AA. Discovery of an Extended Austinoid Biosynthetic Pathway in Aspergillus calidoustus. ACS Chem Biol. 2017 May 19;12(5):1227-1234. doi: 10.1021/acschembio.7b00003. Epub 2017 Mar 15. PMID: 28233494. 9: Itoh E, Shigemoto R, Oinuma KI, Shimizu M, Masuo S, Takaya N. Sirtuin A regulates secondary metabolite production by Aspergillus nidulans. J Gen Appl Microbiol. 2017 Sep 5;63(4):228-235. doi: 10.2323/jgam.2016.11.002. Epub 2017 Jul 1. PMID: 28674377. 10: Guo CJ, Knox BP, Chiang YM, Lo HC, Sanchez JF, Lee KH, Oakley BR, Bruno KS, Wang CC. Molecular genetic characterization of a cluster in A. terreus for biosynthesis of the meroterpenoid terretonin. Org Lett. 2012 Nov 16;14(22):5684-7. doi: 10.1021/ol302682z. Epub 2012 Nov 1. PMID: 23116177; PMCID: PMC3538129. 11: Gaur SS, Annapure US. Untargeted metabolite profiling of Enterococcus villorum SB2, isolated from the vagina of pregnant women, by HR-LCMS. World J Microbiol Biotechnol. 2022 Sep 7;38(12):219. doi: 10.1007/s11274-022-03404-3. PMID: 36070101. 12: Zhang G, Sun S, Zhu T, Lin Z, Gu J, Li D, Gu Q. Antiviral isoindolone derivatives from an endophytic fungus Emericella sp. associated with Aegiceras corniculatum. Phytochemistry. 2011 Aug;72(11-12):1436-42. doi: 10.1016/j.phytochem.2011.04.014. Epub 2011 May 23. PMID: 21601895. 13: Pandit SS, Zheng J, Yin Y, Lorber S, Puel O, Dhingra S, Espeso EA, Calvo AM. Homeobox transcription factor HbxA influences expression of over one thousand genes in the model fungus Aspergillus nidulans. PLoS One. 2023 Jul 21;18(7):e0286271. doi: 10.1371/journal.pone.0286271. PMID: 37478074; PMCID: PMC10361519. 14: Yeh HH, Chang SL, Chiang YM, Bruno KS, Oakley BR, Wu TK, Wang CC. Engineering fungal nonreducing polyketide synthase by heterologous expression and domain swapping. Org Lett. 2013 Feb 15;15(4):756-9. doi: 10.1021/ol303328t. Epub 2013 Jan 31. PMID: 23368695; PMCID: PMC3681297. 15: Szewczyk E, Chiang YM, Oakley CE, Davidson AD, Wang CC, Oakley BR. Identification and characterization of the asperthecin gene cluster of Aspergillus nidulans. Appl Environ Microbiol. 2008 Dec;74(24):7607-12. doi: 10.1128/AEM.01743-08. Epub 2008 Oct 31. PMID: 18978088; PMCID: PMC2607171. 16: Wu MY, Mead ME, Lee MK, Neuhaus GF, Adpressa DA, Martien JI, Son YE, Moon H, Amador-Noguez D, Han KH, Rokas A, Loesgen S, Yu JH, Park HS. Transcriptomic, Protein-DNA Interaction, and Metabolomic Studies of VosA, VelB, and WetA in Aspergillus nidulans Asexual Spores. mBio. 2021 Feb 9;12(1):e03128-20. doi: 10.1128/mBio.03128-20. PMID: 33563821; PMCID: PMC7885118. 17: Thieme KG, Gerke J, Sasse C, Valerius O, Thieme S, Karimi R, Heinrich AK, Finkernagel F, Smith K, Bode HB, Freitag M, Ram AFJ, Braus GH. Velvet domain protein VosA represses the zinc cluster transcription factor SclB regulatory network for Aspergillus nidulans asexual development, oxidative stress response and secondary metabolism. PLoS Genet. 2018 Jul 25;14(7):e1007511. doi: 10.1371/journal.pgen.1007511. Erratum in: PLoS Genet. 2018 Aug 29;14(8):e1007638. doi: 10.1371/journal.pgen.1007638. PMID: 30044771; PMCID: PMC6078315. 18: Alanzi AR, Alajmi MF, Al-Dosari MS, Parvez MK, Alqahtani MJ. In silico exploration of deep-sea fungal metabolites as inhibitor of Ebola and Marburg VP35 and VP40. PLoS One. 2024 Jul 25;19(7):e0307579. doi: 10.1371/journal.pone.0307579. PMID: 39052567; PMCID: PMC11271895. 19: Nielsen ML, Nielsen JB, Rank C, Klejnstrup ML, Holm DK, Brogaard KH, Hansen BG, Frisvad JC, Larsen TO, Mortensen UH. A genome-wide polyketide synthase deletion library uncovers novel genetic links to polyketides and meroterpenoids in Aspergillus nidulans. FEMS Microbiol Lett. 2011 Aug;321(2):157-66. doi: 10.1111/j.1574-6968.2011.02327.x. Epub 2011 Jun 27. PMID: 21658102. 20: Rodríguez-Urra AB, Jiménez C, Nieto MI, Rodríguez J, Hayashi H, Ugalde U. Signaling the induction of sporulation involves the interaction of two secondary metabolites in Aspergillus nidulans. ACS Chem Biol. 2012 Mar 16;7(3):599-606. doi: 10.1021/cb200455u. Epub 2012 Jan 24. PMID: 22234162.