WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 585336
Description: Uvaretin displays growth inhibitory effects against human promyelocytic leukemia HL-60 cells.
MedKoo Cat#: 585336
Chemical Formula: C23H22O5
Exact Mass: 378.1467
Molecular Weight: 378.424
Elemental Analysis: C, 73.00; H, 5.86; O, 21.14
This product is not in stock, which may be available by custom synthesis.
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IUPAC/Chemical Name: 1-[2,4-dihydroxy-3-[(2-hydroxyphenyl)methyl]-6-methoxyphenyl]-3-phenylpropan-1-one
InChi Key: LQHGGFQNRNEFIG-UHFFFAOYSA-N
InChi Code: InChI=1S/C23H22O5/c1-28-21-14-20(26)17(13-16-9-5-6-10-18(16)24)23(27)22(21)19(25)12-11-15-7-3-2-4-8-15/h2-10,14,24,26-27H,11-13H2,1H3
SMILES Code: O=C(C1=C(OC)C=C(O)C(CC2=CC=CC=C2O)=C1O)CCC3=CC=CC=C3
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
The following data is based on the product molecular weight 378.424 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: Nakatani N, Ichimaru M, Moriyasu M, Kato A. Induction of apoptosis in human promyelocytic leukemia cell line HL-60 by C-benzylated dihydrochalcones, uvaretin, isouvaretin and diuvaretin. Biol Pharm Bull. 2005 Jan;28(1):83-6. PubMed PMID: 15635168.
2: Cole JR, Torrance SJ, Wiedhopf RM, Arora SK, Bates RB. Uvaretin, a new antitumor agent from Uvaria acuminata (Annonaceae). J Org Chem. 1976 May 14;41(10):1852-5. PubMed PMID: 1262991.
3: Kongstad KT, Wubshet SG, Kjellerup L, Winther AM, Staerk D. Fungal plasma membrane H⁺-ATPase inhibitory activity of o-hydroxybenzylated flavanones and chalcones from Uvaria chamae P. Beauv. Fitoterapia. 2015 Sep;105:102-6. doi: 10.1016/j.fitote.2015.06.013. Epub 2015 Jun 20. PubMed PMID: 26102180.
4: Dallman J, Lansakara A, Nguyen T, Weeramange C, Hulangamuwa W, Rafferty RJ. The winding road of the uvaretin class of natural products: from total synthesis to bioactive agent discovery. Medchemcomm. 2019 Jun 11;10(8):1420-1431. doi: 10.1039/c9md00052f. eCollection 2019 Aug 1. PubMed PMID: 31673309; PubMed Central PMCID: PMC6786243.
5: Hufford CD, Lasswell WL Jr. Uvaretin and isouvaretin. Two novel cytotoxic c-benzylflavanones from uvaria chamae L. J Org Chem. 1976 Apr 2;41(7):1297-8. PubMed PMID: 1255298.
6: Ichimaru M, Nakatani N, Takahashi T, Nishiyama Y, Moriyasu M, Kato A, Mathenge SG, Juma FD, Nganga JN. Cytotoxic C-benzylated dihydrochalcones from Uvaria acuminata. Chem Pharm Bull (Tokyo). 2004 Jan;52(1):138-41. PubMed PMID: 14709883.
7: Makangara JJ, Jonker SA, Nkunya MH. A novel phenanthrenolide and C-benzyl dihydrochalcones from Uvaria puguensis. Nat Prod Lett. 2002 Aug;16(4):267-72. PubMed PMID: 12168763.
8: Nkunya MH, Weenen H, Bray DH, Mgani QA, Mwasumbi LB. Antimalarial activity of Tanzanian plants and their active constituents: the genus Uvaria. Planta Med. 1991 Aug;57(4):341-3. PubMed PMID: 1775574.
9: Weeramange C, Lansakara A, Dallman J, Nguyen T, Hulangamuwa W, Rafferty RJ. New methods to assess 6-thiopurine toxicity and expanding its therapeutic application to pancreatic cancer via small molecule potentiators. Medchemcomm. 2019 Mar 18;10(5):717-725. doi: 10.1039/c9md00010k. eCollection 2019 May 1. PubMed PMID: 31191862; PubMed Central PMCID: PMC6533796.