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MedKoo Cat#: 461292 | Name: Alaternin

Description:

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

Alaternin is an anthraquinone that has shown to competitively inhibited PTP1B, and showed mixed-type inhibition against α-glucosidase.

Chemical Structure

Alaternin
Alaternin
CAS#39723-40-5

Theoretical Analysis

MedKoo Cat#: 461292

Name: Alaternin

CAS#: 39723-40-5

Chemical Formula: C34H42O19

Exact Mass: 754.2320

Molecular Weight: 754.69

Elemental Analysis: C, 54.11; H, 5.61; O, 40.28

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
Alaternin; Catharticin;
IUPAC/Chemical Name
3-(((2S,3R,4S,5R,6R)-6-((((2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
InChi Key
MQMTVWHXCSRCER-BZPRNGGBSA-N
InChi Code
InChI=1S/C34H42O19/c1-11-20(37)24(41)26(43)33(49-11)52-30-21(38)12(2)48-32(28(30)45)47-10-18-22(39)25(42)27(44)34(51-18)53-31-23(40)19-16(36)8-15(46-3)9-17(19)50-29(31)13-4-6-14(35)7-5-13/h4-9,11-12,18,20-22,24-28,30,32-39,41-45H,10H2,1-3H3/t11-,12-,18+,20-,21-,22-,24+,25-,26+,27+,28+,30+,32+,33-,34-/m0/s1
SMILES Code
O=C1C(O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO[C@H]3[C@H](O)[C@H](O[C@H]4[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4)[C@@H](O)[C@H](C)O3)O2)=C(C5=CC=C(O)C=C5)OC6=C1C(O)=CC(OC)=C6
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 754.69 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: Jung HA, Ali MY, Choi JS. Promising Inhibitory Effects of Anthraquinones, Naphthopyrone, and Naphthalene Glycosides, from Cassia obtusifolia on α-Glucosidase and Human Protein Tyrosine Phosphatases 1B. Molecules. 2016 Dec 27;22(1). pii: E28. doi: 10.3390/molecules22010028. PubMed PMID: 28035984. 2: Lu TM, Ko HH. A new anthraquinone glycoside from Rhamnus nakaharai and anti-tyrosinase effect of 6-methoxysorigenin. Nat Prod Res. 2016 Feb 1:1-7. [Epub ahead of print] PubMed PMID: 26828875. 3: Shin BY, Kim DH, Hyun SK, Jung HA, Kim JM, Park SJ, Kim SY, Cheong JH, Choi JS, Ryu JH. Alaternin attenuates delayed neuronal cell death induced by transient cerebral hypoperfusion in mice. Food Chem Toxicol. 2010 Jun;48(6):1528-36. doi: 10.1016/j.fct.2010.03.020. Epub 2010 Mar 19. PubMed PMID: 20304026. 4: Park TH, Kim DH, Kim CH, Jung HA, Choi JS, Lee JW, Chung HY. Peroxynitrite scavenging mode of alaternin isolated from Cassia tora. J Pharm Pharmacol. 2004 Oct;56(10):1315-21. PubMed PMID: 15482647. 5: Jung HA, Chung HY, Yokozawa T, Kim YC, Hyun SK, Choi JS. Alaternin and emodin with hydroxyl radical inhibitory and/or scavenging activities and hepatoprotective activity on tacrine-induced cytotoxicity in HepG2 cells. Arch Pharm Res. 2004 Sep;27(9):947-53. PubMed PMID: 15473666. 6: Choi JS, Chung HY, Jung HA, Park HJ, Yokozawa T. Comparative evaluation of antioxidant potential of alaternin (2-hydroxyemodin) and emodin. J Agric Food Chem. 2000 Dec;48(12):6347-51. PubMed PMID: 11312806. 7: Choi JS, Lee HJ, Kang SS. Alaternin, cassiaside and rubrofusarin gentiobioside, radical scavenging principles from the seeds of Cassia tora on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. Arch Pharm Res. 1994 Dec;17(6):462-6. PubMed PMID: 10319159. 8: Jung HA, Ali MY, Jung HJ, Jeong HO, Chung HY, Choi JS. Inhibitory activities of major anthraquinones and other constituents from Cassia obtusifolia against β-secretase and cholinesterases. J Ethnopharmacol. 2016 Sep 15;191:152-160. doi: 10.1016/j.jep.2016.06.037. Epub 2016 Jun 15. PubMed PMID: 27321278. 9: Zhao C, Meng F, Geng L, Zhao X, Zhou H, Zhang Y, Qin S. Cardiac-protective effects and the possible mechanisms of alatamine during acute myocardial ischemia. Can J Physiol Pharmacol. 2016 Apr;94(4):433-40. doi: 10.1139/cjpp-2015-0246. Epub 2015 Oct 8. PubMed PMID: 26863576. 10: Lee HJ, Jung JH, Kang SS, Choi JS. A rubrofusarin gentiobioside isomer from roastedCassia tora. Arch Pharm Res. 1997 Oct;20(5):513-5. doi: 10.1007/BF02973951. PubMed PMID: 18982501. 11: Hyun SK, Lee H, Kang SS, Chung HY, Choi JS. Inhibitory activities of Cassia tora and its anthraquinone constituents on angiotensin-converting enzyme. Phytother Res. 2009 Feb;23(2):178-84. doi: 10.1002/ptr.2579. PubMed PMID: 18803227. 12: Masuda T, Haraikawa K, Morooka N, Nakano S, Ueno Y. 2-Hydroxyemodin, an active metabolite of emodin in the hepatic microsomes of rats. Mutat Res. 1985 May;149(3):327-32. PubMed PMID: 3887143. 13: Kodama M, Kamioka Y, Nakayama T, Nagata C, Morooka N, Ueno Y. Generation of free radical and hydrogen peroxide from 2-hydroxyemodin, a direct-acting mutagen, and DNA strand breaks by active oxygen. Toxicol Lett. 1987 Jul;37(2):149-56. PubMed PMID: 3299878.