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MedKoo Cat#: 341281 | Name: Yuanhuanin

Description:

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

Yuanhuanin is a biochemical.

Chemical Structure

Yuanhuanin
Yuanhuanin
CAS#83133-14-6

Theoretical Analysis

MedKoo Cat#: 341281

Name: Yuanhuanin

CAS#: 83133-14-6

Chemical Formula: C22H22O11

Exact Mass: 462.1162

Molecular Weight: 462.41

Elemental Analysis: C, 57.14; H, 4.80; O, 38.06

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 #
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Synonym
Yuanhuanin;
IUPAC/Chemical Name
3'-Hydroxygenkwanin 5-O-beta-glucoside
InChi Key
ZXVSQQSRCKKYLS-MIUGBVLSSA-N
InChi Code
InChI=1S/C22H22O11/c1-30-10-5-15-18(13(26)7-14(31-15)9-2-3-11(24)12(25)4-9)16(6-10)32-22-21(29)20(28)19(27)17(8-23)33-22/h2-7,17,19-25,27-29H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1
SMILES Code
O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=C1C(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)=CC(OC)=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
>2 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 462.41 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: Han BS, Minh NV, Choi HY, Byun JS, Kim WG. Daphnane and Phorbol Diterpenes, Anti-neuroinflammatory Compounds with Nurr1 Activation from the Roots and Stems of Daphne genkwa. Biol Pharm Bull. 2017;40(12):2205-2211. doi: 10.1248/bpb.b17-00641. PubMed PMID: 29199243. 2: Li M, Liu X, Cai H, Shen Z, Xu L, Li W, Wu L, Duan J, Chen Z. Validation and Application of an Ultra High-Performance Liquid Chromatography Tandem Mass Spectrometry Method for Yuanhuacine Determination in Rat Plasma after Pulmonary Administration: Pharmacokinetic Evaluation of a New Drug Delivery System. Molecules. 2016 Dec 16;21(12). pii: E1733. doi: 10.3390/molecules21121733. PubMed PMID: 27999290. 3: Han BS, Kim KS, Kim YJ, Jung HY, Kang YM, Lee KS, Sohn MJ, Kim CH, Kim KS, Kim WG. Daphnane Diterpenes from Daphne genkwa Activate Nurr1 and Have a Neuroprotective Effect in an Animal Model of Parkinson's Disease. J Nat Prod. 2016 Jun 24;79(6):1604-9. doi: 10.1021/acs.jnatprod.6b00110. Epub 2016 May 26. PubMed PMID: 27228307; PubMed Central PMCID: PMC5635821. 4: Li L, Yin FZ, Lu TL, Guan HY, Cai BC. [Fingerprint of Vinegar Processed Genkwa Flos Based on Improving Euclidean Distance]. Zhong Yao Cai. 2015 Jun;38(6):1168-71. Chinese. PubMed PMID: 26762055. 5: Kang JI, Hong JY, Lee HJ, Bae SY, Jung C, Park HJ, Lee SK. Anti-Tumor Activity of Yuanhuacine by Regulating AMPK/mTOR Signaling Pathway and Actin Cytoskeleton Organization in Non-Small Cell Lung Cancer Cells. PLoS One. 2015 Dec 11;10(12):e0144368. doi: 10.1371/journal.pone.0144368. eCollection 2015. PubMed PMID: 26656173; PubMed Central PMCID: PMC4676678. 6: Zhang R, Wang Y, Li J, Jin H, Song S, Huang C. The Chinese herb isolate yuanhuacine (YHL-14) induces G2/M arrest in human cancer cells by up-regulating p21 protein expression through an p53 protein-independent cascade. J Biol Chem. 2014 Mar 7;289(10):6394-403. doi: 10.1074/jbc.M113.513960. Epub 2014 Jan 22. PubMed PMID: 24451377; PubMed Central PMCID: PMC3945306. 7: Chen YY, Qian DW, Shang EX, Qian YF, Liu P, Su SL, Guo JM, Tang YP, Duan JA. [The incompatibility mechanism based on the interaction of multiple-components for Flos Genkwa and Radix et Rhizoma Glycyrrhizae]. Yao Xue Xue Bao. 2012 Aug;47(8):1043-8. Chinese. PubMed PMID: 23162902. 8: Hong JY, Nam JW, Seo EK, Lee SK. Daphnane diterpene esters with anti-proliferative activities against human lung cancer cells from Daphne genkwa. Chem Pharm Bull (Tokyo). 2010 Feb;58(2):234-7. PubMed PMID: 20118586. 9: Zhang S, Gao X, Shen K, Yang P, Ju X. Evaluation of poly(D,L-lactide-co-glycolide) microspheres for the lung-targeting of yuanhuacine, a novel DNA topoisomerase I inhibitor. J Drug Target. 2009 May;17(4):286-93. doi: 10.1080/10611860902737912. PubMed PMID: 19558356. 10: Zhang SX, Yang PW, Zhang DC, Dong WQ, Zhang FH, Sun YM. Pharmacokinetics, tissue distribution, and metabolism of novel DNA topoisomerase I inhibitor yuanhuacine in rabbit. Xenobiotica. 2009 Mar;39(3):273-81. doi: 10.1080/00498250802715987. PubMed PMID: 19280526. 11: Park BY, Min BS, Ahn KS, Kwon OK, Joung H, Bae KH, Lee HK, Oh SR. Daphnane diterpene esters isolated from flower buds of Daphne genkwa induce apoptosis in human myelocytic HL-60 cells and suppress tumor growth in Lewis lung carcinoma (LLC)-inoculated mouse model. J Ethnopharmacol. 2007 May 22;111(3):496-503. Epub 2006 Dec 27. PubMed PMID: 17241759. 12: Zhang S, Li X, Zhang F, Yang P, Gao X, Song Q. Preparation of yuanhuacine and relative daphne diterpene esters from Daphne genkwa and structure-activity relationship of potent inhibitory activity against DNA topoisomerase I. Bioorg Med Chem. 2006 Jun 1;14(11):3888-95. Epub 2006 Feb 20. PubMed PMID: 16488610. 13: Yuan S, Wang Z, Xia K. [Comprehensive evaluation and practical confirmation on processing technology of Daphne genkwa Sieb. et Zucc]. Zhongguo Zhong Yao Za Zhi. 1999 Aug;24(8):464-5, 510. Chinese. PubMed PMID: 12205864. 14: Zhang J, Wang Y, Sun C. [Quality of processed samples of Daphne genkwa Sieb. et Zucc]. Zhongguo Zhong Yao Za Zhi. 1997 Feb;22(2):85-7, 127. Chinese. PubMed PMID: 10743197. 15: Yuan S, Zhang B, Xia K. [HPLC analysis of mimic vinegar-processed yuanhuacine]. Zhongguo Zhong Yao Za Zhi. 1996 Aug;21(8):469-71, 510. Chinese. PubMed PMID: 9642406. 16: Zhang BX, Yuan XT, Xia K, Li JH. [Determination of yuanhuacine in Daphne genkwa Sieb. et Zucc. by HPLC]. Zhongguo Zhong Yao Za Zhi. 1994 Sep;19(9):551-2, 575. Chinese. PubMed PMID: 7811369. 17: Yan R, Li PQ. [Preparation of yuanhuacine by low pressure column chromatography]. Zhongguo Zhong Yao Za Zhi. 1993 Dec;18(12):729-30, 763. Chinese. PubMed PMID: 8011083. 18: Zhang DC, Cao CX, Zhang CJ, Zhou BN. Yuanhuacin A is a selective antagonist of phorbol ester receptor in protein kinase C. Sci China B. 1993 Jul;36(7):803-8. PubMed PMID: 8216740. 19: Li PQ. [Yuanhuacin film for menstruation induction and termination of early pregnancy: analysis of 382]. Zhonghua Fu Chan Ke Za Zhi. 1989 Jul;24(4):231-3, 253. Chinese. PubMed PMID: 2559832. 20: Wang SX. [Clinical study of termination of early pregnancy by administration of yuanhuacine in combination with testosterone propionate]. Zhonghua Fu Chan Ke Za Zhi. 1988 Sep;23(5):296-8, 318. Chinese. PubMed PMID: 3250813.