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MedKoo Cat#: 593043 | Name: Atranorin
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Description:

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

Atranorin, a compound with the depside structure, is one of the most common lichen secondary metabolites, characteristic for numerous lichen families but rarely found in some mosses and higher plants. The literature describes anti-inflammatory, analgesic, as well as wound healing, antibacterial, antifungal, cytotoxic, antioxidant, antiviral, and immunomodulatory activities of the depside. Furthermore, lack of toxicity of atranorin was confirmed in the animals' in vivo assays.

Chemical Structure

Atranorin
Atranorin
CAS#479-20-9

Theoretical Analysis

MedKoo Cat#: 593043

Name: Atranorin

CAS#: 479-20-9

Chemical Formula: C19H18O8

Exact Mass: 374.1002

Molecular Weight: 374.35

Elemental Analysis: Chemical Formula: Exact Mass: Molecular Weight: Elemental Analysis: C, 60.96; H, 4.85; O, 34.19

Price and Availability

Size Price Availability Quantity
5mg USD 455.00 2 Weeks
10mg USD 770.00 2 Weeks
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Related CAS #
No Data
Synonym
Atranorin; NSC 87512; NSC87512; NSC-87512; NSC 249980; NSC249980; NSC-249980; NSC 685591; NSC685591; NSC-685591
IUPAC/Chemical Name
3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate
InChi Key
YLOYKYXNDHOHHT-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H18O8/c1-8-5-12(21)11(7-20)17(23)15(8)19(25)27-13-6-9(2)14(18(24)26-4)16(22)10(13)3/h5-7,21-23H,1-4H3
SMILES Code
O=C(OC1=CC(C)=C(C(OC)=O)C(O)=C1C)C2=C(C)C=C(O)C(C=O)=C2O
Appearance
Solid powder
Purity
>95% (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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 374.35 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: Shukla I, Azmi L, Gupta SS, Upreti DK, Rao CV. Melioration of anti-hepatotoxic effect by Lichen rangiferinus against alcohol induced liver damage in rats. J Ayurveda Integr Med. 2018 Jan 29. pii: S0975-9476(17)30047-5. doi: 10.1016/j.jaim.2017.08.007. [Epub ahead of print] PubMed PMID: 29395895. 2: Woo JJ, Lőkös L, Farkas E, Park CH, Hur JS. Cryptothecia austrocoreana (Arthoniales, Arthoniaceae), a New Species from South Korea. Mycobiology. 2017 Dec;45(4):338-343. doi: 10.5941/MYCO.2017.45.4.338. Epub 2017 Dec 31. PubMed PMID: 29371801; PubMed Central PMCID: PMC5780365. 3: Stojanović G, Zlatanović I, Zrnzević I, Stanković M, Stankov Jovanović V, Zlatković B. Hypogymnia tubulosa extracts: chemical profile and biological activities. Nat Prod Res. 2017 Sep 13:1-5. doi: 10.1080/14786419.2017.1375926. [Epub ahead of print] PubMed PMID: 28901170. 4: Paluszczak J, Kleszcz R, Studzińska-Sroka E, Krajka-Kuźniak V. Lichen-derived caperatic acid and physodic acid inhibit Wnt signaling in colorectal cancer cells. Mol Cell Biochem. 2018 Apr;441(1-2):109-124. doi: 10.1007/s11010-017-3178-7. Epub 2017 Sep 8. PubMed PMID: 28887754; PubMed Central PMCID: PMC5843697. 5: Zhou R, Yang Y, Park SY, Nguyen TT, Seo YW, Lee KH, Lee JH, Kim KK, Hur JS, Kim H. The lichen secondary metabolite atranorin suppresses lung cancer cell motility and tumorigenesis. Sci Rep. 2017 Aug 15;7(1):8136. doi: 10.1038/s41598-017-08225-1. PubMed PMID: 28811522; PubMed Central PMCID: PMC5557893. 6: Studzinska-Sroka E, Galanty A, Bylka W. Atranorin - An Interesting Lichen Secondary Metabolite. Mini Rev Med Chem. 2017;17(17):1633-1645. doi: 10.2174/1389557517666170425105727. Review. PubMed PMID: 28443519. 7: Galanty A, Koczurkiewicz P, Wnuk D, Paw M, Karnas E, Podolak I, Węgrzyn M, Borusiewicz M, Madeja Z, Czyż J, Michalik M. Usnic acid and atranorin exert selective cytostatic and anti-invasive effects on human prostate and melanoma cancer cells. Toxicol In Vitro. 2017 Apr;40:161-169. doi: 10.1016/j.tiv.2017.01.008. Epub 2017 Jan 14. PubMed PMID: 28095330. 8: Cardile V, Graziano ACE, Avola R, Piovano M, Russo A. Potential anticancer activity of lichen secondary metabolite physodic acid. Chem Biol Interact. 2017 Feb 1;263:36-45. doi: 10.1016/j.cbi.2016.12.007. Epub 2016 Dec 21. PubMed PMID: 28012710. 9: Reddy RG, Veeraval L, Maitra S, Chollet-Krugler M, Tomasi S, Dévéhat FL, Boustie J, Chakravarty S. Lichen-derived compounds show potential for central nervous system therapeutics. Phytomedicine. 2016 Nov 15;23(12):1527-1534. doi: 10.1016/j.phymed.2016.08.010. Epub 2016 Aug 31. PubMed PMID: 27765373. 10: Goga M, Antreich SJ, Bačkor M, Weckwerth W, Lang I. Lichen secondary metabolites affect growth of Physcomitrella patens by allelopathy. Protoplasma. 2017 May;254(3):1307-1315. doi: 10.1007/s00709-016-1022-7. Epub 2016 Sep 19. PubMed PMID: 27645140. 11: Ristić S, Ranković B, Kosanić M, Stanojković T, Stamenković S, Vasiljević P, Manojlović I, Manojlović N. Phytochemical study and antioxidant, antimicrobial and anticancer activities of Melanelia subaurifera and Melanelia fuliginosa lichens. J Food Sci Technol. 2016 Jun;53(6):2804-16. doi: 10.1007/s13197-016-2255-3. Epub 2016 Jun 22. PubMed PMID: 27478237; PubMed Central PMCID: PMC4951434. 12: Ristic S, Rankovic B, Kosanić M, Stamenkovic S, Stanojković T, Sovrlić M, Manojlović N. Biopharmaceutical Potential of Two Ramalina Lichens and their Metabolites. Curr Pharm Biotechnol. 2016;17(7):651-8. PubMed PMID: 27033512. 13: Nakashima K, Tanabe H, Fujii-Kuriyama Y, Hayashi H, Inoue M. Atranorin and lecanoric acid antagonize TCDD-induced xenobiotic response element-driven activity, but not xenobiotic response element-independent activity. J Nat Med. 2016 Jul;70(3):476-82. doi: 10.1007/s11418-016-0983-3. Epub 2016 Mar 15. PubMed PMID: 26979434. 14: Solár P, Hrčková G, Koptašíková L, Velebný S, Solárová Z, Bačkor M. Murine breast carcinoma 4T1 cells are more sensitive to atranorin than normal epithelial NMuMG cells in vitro: Anticancer and hepatoprotective effects of atranorin in vivo. Chem Biol Interact. 2016 Apr 25;250:27-37. doi: 10.1016/j.cbi.2016.03.012. Epub 2016 Mar 8. PubMed PMID: 26969521. 15: Komaty S, Letertre M, Dang HD, Jungnickel H, Laux P, Luch A, Carrié D, Merdrignac-Conanec O, Bazureau JP, Gauffre F, Tomasi S, Paquin L. Sample preparation for an optimized extraction of localized metabolites in lichens: Application to Pseudevernia furfuracea. Talanta. 2016 Apr 1;150:525-30. doi: 10.1016/j.talanta.2015.12.081. Epub 2015 Dec 31. PubMed PMID: 26838439. 16: Shukla V, Patel DK, Bajpai R, Semwal M, Upreti DK. Ecological implication of variation in the secondary metabolites in Parmelioid lichens with respect to altitude. Environ Sci Pollut Res Int. 2016 Jan;23(2):1391-7. doi: 10.1007/s11356-015-5311-z. Epub 2015 Sep 15. PubMed PMID: 26370809. 17: Latkowska E, Bober B, Chrapusta E, Adamski M, Kaminski A, Bialczyk J. Secondary metabolites of the lichen Hypogymnia physodes (L.) Nyl. and their presence in spruce (Picea abies (L.) H. Karst.) bark. Phytochemistry. 2015 Oct;118:116-23. doi: 10.1016/j.phytochem.2015.08.016. Epub 2015 Sep 2. PubMed PMID: 26342621. 18: Vu TH, Le Lamer AC, Lalli C, Boustie J, Samson M, Lohézic-Le Dévéhat F, Le Seyec J. Depsides: lichen metabolites active against hepatitis C virus. PLoS One. 2015 Mar 20;10(3):e0120405. doi: 10.1371/journal.pone.0120405. eCollection 2015. PubMed PMID: 25793970; PubMed Central PMCID: PMC4368788. 19: Gaikwad S, Verma N, Sharma BO, Behera BC. Growth promoting effects of some lichen metabolites on probiotic bacteria. J Food Sci Technol. 2014 Oct;51(10):2624-31. doi: 10.1007/s13197-012-0785-x. Epub 2012 Aug 2. PubMed PMID: 25328204; PubMed Central PMCID: PMC4190253. 20: Truong TL, Nga VT, Huy DT, Chi HB, Phung NK. A new depside from Usnea aciculifera growing in Vietnam. Nat Prod Commun. 2014 Aug;9(8):1179-80. PubMed PMID: 25233603.