MedKoo Cat#: 585336 | Name: Uvaretin

Description:

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

Uvaretin displays growth inhibitory effects against human promyelocytic leukemia HL-60 cells.

Chemical Structure

Uvaretin
Uvaretin
CAS#58449-06-2

Theoretical Analysis

MedKoo Cat#: 585336

Name: Uvaretin

CAS#: 58449-06-2

Chemical Formula: C23H22O5

Exact Mass: 378.1467

Molecular Weight: 378.42

Elemental Analysis: C, 73.00; H, 5.86; O, 21.14

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
Uvaretin
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 378.42 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: 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.