MedKoo Cat#: 565770 | Name: Atromentin

Description:

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

Atromentin is a natural chemical compound found in Agaricomycetes fungi in the orders Agaricales and Thelephorales. It can also be prepared by laboratory synthesis. Chemically, it is a polyphenol and a benzoquinone.

Chemical Structure

Atromentin
Atromentin
CAS#519-67-5

Theoretical Analysis

MedKoo Cat#: 565770

Name: Atromentin

CAS#: 519-67-5

Chemical Formula: C18H12O6

Exact Mass: 324.0634

Molecular Weight: 324.29

Elemental Analysis: C, 66.67; H, 3.73; O, 29.60

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
NSC-187730; NSC 187730; NSC187730
IUPAC/Chemical Name
2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione
InChi Key
FKQQKMGWCJGUCS-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H12O6/c19-11-5-1-9(2-6-11)13-15(21)17(23)14(18(24)16(13)22)10-3-7-12(20)8-4-10/h1-8,19-21,24H
SMILES Code
O=C1C(O)=C(C2=CC=C(O)C=C2)C(C(O)=C1C3=CC=C(O)C=C3)=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 324.29 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: Zheng CJ, Sohn MJ, Kim WG. Atromentin and leucomelone, the first inhibitors specific to enoyl-ACP reductase (FabK) of Streptococcus pneumoniae. J Antibiot (Tokyo). 2006 Dec;59(12):808-12. PubMed PMID: 17323650. 2: Kim JH, Lee CH. Atromentin-induced apoptosis in human leukemia U937 cells. J Microbiol Biotechnol. 2009 Sep;19(9):946-50. PubMed PMID: 19809251. 3: Schneider P, Bouhired S, Hoffmeister D. Characterization of the atromentin biosynthesis genes and enzymes in the homobasidiomycete Tapinella panuoides. Fungal Genet Biol. 2008 Nov;45(11):1487-96. doi: 10.1016/j.fgb.2008.08.009. Epub 2008 Sep 6. PubMed PMID: 18805498. 4: Geib E, Baldeweg F, Doerfer M, Nett M, Brock M. Cross-Chemistry Leads to Product Diversity from Atromentin Synthetases in Aspergilli from Section Nigri. Cell Chem Biol. 2019 Feb 21;26(2):223-234.e6. doi: 10.1016/j.chembiol.2018.10.021. Epub 2018 Dec 6. PubMed PMID: 30527997. 5: Tauber JP, Gallegos-Monterrosa R, Kovács ÁT, Shelest E, Hoffmeister D. Dissimilar pigment regulation in Serpula lacrymans and Paxillus involutus during inter-kingdom interactions. Microbiology. 2018 Jan;164(1):65-77. doi: 10.1099/mic.0.000582. Epub 2017 Dec 5. PubMed PMID: 29205129. 6: Khanna JM, Malone MH, Euler KL, Brady LR. Atromentin, anticoagulant from Hydnellum diabolus. J Pharm Sci. 1965 Jul;54(7):1016-20. PubMed PMID: 5862512. 7: Ye YQ, Koshino H, Abe N, Nakamura T, Hashizume D, Takahashi S. Synthesis of atromentin and its O-alkylated natural products. Biosci Biotechnol Biochem. 2010;74(11):2342-4. Epub 2010 Nov 7. PubMed PMID: 21071857. 8: Tauber JP, Schroeckh V, Shelest E, Brakhage AA, Hoffmeister D. Bacteria induce pigment formation in the basidiomycete Serpula lacrymans. Environ Microbiol. 2016 Dec;18(12):5218-5227. doi: 10.1111/1462-2920.13558. Epub 2016 Oct 24. PubMed PMID: 27699944. 9: Sullivan G, Garrett RD, Lenehan RF. Occurrence of atromentin and thelephoric acid in cultures of Clitocybe subilludens. J Pharm Sci. 1971 Nov;60(11):1727-9. PubMed PMID: 4332377. 10: Dellafiora L, Aichinger G, Geib E, Sánchez-Barrionuevo L, Brock M, Cánovas D, Dall'Asta C, Marko D. Hybrid in silico/in vitro target fishing to assign function to "orphan" compounds of food origin - The case of the fungal metabolite atromentin. Food Chem. 2019 Jan 1;270:61-69. doi: 10.1016/j.foodchem.2018.07.027. Epub 2018 Jul 4. PubMed PMID: 30174092. 11: Braesel J, Götze S, Shah F, Heine D, Tauber J, Hertweck C, Tunlid A, Stallforth P, Hoffmeister D. Three Redundant Synthetases Secure Redox-Active Pigment Production in the Basidiomycete Paxillus involutus. Chem Biol. 2015 Oct 22;22(10):1325-34. doi: 10.1016/j.chembiol.2015.08.016. PubMed PMID: 26496685. 12: Sullivan G, Guess WL. Atromentin: a smooth muscle stimulant in Clitocybe subilludens. Lloydia. 1969 Mar;32(1):72-5. PubMed PMID: 5815216. 13: Intaraudom C, Bunbamrung N, Dramae A, Boonyuen N, Kongsaeree P, Srichomthong K, Supothina S, Pittayakhajonwut P. Terphenyl derivatives and drimane - Phathalide/isoindolinones from Hypoxylon fendleri BCC32408. Phytochemistry. 2017 Jul;139:8-17. doi: 10.1016/j.phytochem.2017.03.008. Epub 2017 Apr 3. PubMed PMID: 28384525. 14: Hühner E, Backhaus K, Kraut R, Li SM. Production of α-keto carboxylic acid dimers in yeast by overexpression of NRPS-like genes from Aspergillus terreus. Appl Microbiol Biotechnol. 2018 Feb;102(4):1663-1672. doi: 10.1007/s00253-017-8719-1. Epub 2018 Jan 5. PubMed PMID: 29305695. 15: Wackler B, Lackner G, Chooi YH, Hoffmeister D. Characterization of the Suillus grevillei quinone synthetase GreA supports a nonribosomal code for aromatic α-keto acids. Chembiochem. 2012 Aug 13;13(12):1798-804. doi: 10.1002/cbic.201200187. Epub 2012 Jun 22. PubMed PMID: 22730234. 16: Brewer D, Jen WC, Jones GA, Taylor A. The antibacterial activity of some naturally occurring 2,5-dihydroxy-1,4-benzoquinones. Can J Microbiol. 1984 Aug;30(8):1068-72. PubMed PMID: 6541963. 17: Onose J, Xie C, Ye YQ, Sugaya K, Takahashi S, Koshino H, Yasunaga K, Abe N, Yoshikawa K. Vialinin A, a novel potent inhibitor of TNF-alpha production from RBL-2H3 cells. Biol Pharm Bull. 2008 May;31(5):831-3. PubMed PMID: 18451502. 18: Hu L, Liu JK. p-Terphenyls from the basidiomycete Thelephora aurantiotincta. Z Naturforsch C. 2003 May-Jun;58(5-6):452-4. PubMed PMID: 12872944. 19: Ngoc Quang D, Hashimoto T, Hitaka Y, Tanaka M, Nukada M, Yamamoto I, Asakawa Y. Thelephantins D-H: five p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta. Phytochemistry. 2003 Aug;63(8):919-24. PubMed PMID: 12895540.