Orientin | CAS#28608-75-5 | neuroprotective

MedKoo Cat#: 584960 | Name: Orientin

Description:

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

Orientin has neuroprotective effects.

Chemical Structure

Orientin

CAS#28608-75-5

Theoretical Analysis

MedKoo Cat#: 584960

Name: Orientin

CAS#: 28608-75-5

Chemical Formula: C21H20O11

Exact Mass: 448.1006

Molecular Weight: 448.38

Elemental Analysis: C, 56.25; H, 4.50; O, 39.25

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Orientin; Lutexin

IUPAC/Chemical Name

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-

InChi Key

PLAPMLGJVGLZOV-VPRICQMDSA-N

InChi Code

InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1

SMILES Code

O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=C([C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)C(O)=CC(O)=C13

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 448.38 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: Zhao N, Sun Q, Song Y, Wang L, Zhang T, Meng F. Comparative pharmacokinetics study of orientin in rat plasma by UHPLC-MS/MS after intravenous administration of single orientin and Trollius chinensis Bunge extract. Biomed Chromatogr. 2018 Apr;32(4). doi: 10.1002/bmc.4142. Epub 2017 Dec 26. PubMed PMID: 29148582. 2: Wang X, An F, Wang S, An Z, Wang S. Orientin Attenuates Cerebral Ischemia/Reperfusion Injury in Rat Model through the AQP-4 and TLR4/NF-κB/TNF-α Signaling Pathway. J Stroke Cerebrovasc Dis. 2017 Oct;26(10):2199-2214. doi: 10.1016/j.jstrokecerebrovasdis.2017.05.002. Epub 2017 Jun 20. PubMed PMID: 28645524. 3: Tian T, Zeng J, Zhao G, Zhao W, Gao S, Liu L. Neuroprotective effects of orientin on oxygen-glucose deprivation/reperfusion-induced cell injury in primary culture of rat cortical neurons. Exp Biol Med (Maywood). 2018 Jan;243(1):78-86. doi: 10.1177/1535370217737983. Epub 2017 Oct 26. PubMed PMID: 29073777; PubMed Central PMCID: PMC5788155. 4: Bae JS. Inhibitory Effect of Orientin on Secretory Group IIA Phospholipase A2. Inflammation. 2015 Aug;38(4):1631-8. doi: 10.1007/s10753-015-0139-8. PubMed PMID: 25687642. 5: Thangaraj K, Vaiyapuri M. Orientin, a C-glycosyl dietary flavone, suppresses colonic cell proliferation and mitigates NF-κB mediated inflammatory response in 1,2-dimethylhydrazine induced colorectal carcinogenesis. Biomed Pharmacother. 2017 Dec;96:1253-1266. doi: 10.1016/j.biopha.2017.11.088. Epub 2017 Dec 2. PubMed PMID: 29198745. 6: Yadav M, Song F, Huang J, Chakravarti A, Jacob NK. Ocimum flavone Orientin as a countermeasure for thrombocytopenia. Sci Rep. 2018 Mar 22;8(1):5075. doi: 10.1038/s41598-018-23419-x. PubMed PMID: 29567949; PubMed Central PMCID: PMC5864743. 7: Wang S, Yu Y, Feng Y, Zou F, Zhang X, Huang J, Zhang Y, Zheng X, Huang XF, Zhu Y, Liu Y. Protective effect of the orientin on noise-induced cognitive impairments in mice. Behav Brain Res. 2016 Jan 1;296:290-300. doi: 10.1016/j.bbr.2015.09.024. Epub 2015 Sep 21. PubMed PMID: 26392065. 8: Liu Y, Lan N, Ren J, Wu Y, Wang ST, Huang XF, Yu Y. Orientin improves depression-like behavior and BDNF in chronic stressed mice. Mol Nutr Food Res. 2015 Jun;59(6):1130-42. doi: 10.1002/mnfr.201400753. Epub 2015 Apr 29. Erratum in: Mol Nutr Food Res. 2015 Jul;59(7):1411. PubMed PMID: 25788013. 9: Koeppen BH. C-Glycosylflavonoids. The chemistry of orientin and iso-orientin. Biochem J. 1965 Nov;97(2):444-8. PubMed PMID: 16749149; PubMed Central PMCID: PMC1264660. 10: An F, Wang S, Tian Q, Zhu D. Effects of orientin and vitexin from Trollius chinensis on the growth and apoptosis of esophageal cancer EC-109 cells. Oncol Lett. 2015 Oct;10(4):2627-2633. Epub 2015 Aug 18. PubMed PMID: 26622901; PubMed Central PMCID: PMC4580036. 11: Guo D, Hu X, Zhang H, Lu C, Cui G, Luo X. Orientin and neuropathic pain in rats with spinal nerve ligation. Int Immunopharmacol. 2018 May;58:72-79. doi: 10.1016/j.intimp.2018.03.013. Epub 2018 Mar 17. PubMed PMID: 29558662. 12: Nash LA, Sullivan PJ, Peters SJ, Ward WE. Rooibos flavonoids, orientin and luteolin, stimulate mineralization in human osteoblasts through the Wnt pathway. Mol Nutr Food Res. 2015 Mar;59(3):443-53. doi: 10.1002/mnfr.201400592. Epub 2015 Jan 14. PubMed PMID: 25488131. 13: Law BN, Ling AP, Koh RY, Chye SM, Wong YP. Neuroprotective effects of orientin on hydrogen peroxide induced apoptosis in SH SY5Y cells. Mol Med Rep. 2014 Mar;9(3):947-54. doi: 10.3892/mmr.2013.1878. Epub 2013 Dec 24. PubMed PMID: 24366367. 14: Lee W, Ku SK, Bae JS. Vascular barrier protective effects of orientin and isoorientin in LPS-induced inflammation in vitro and in vivo. Vascul Pharmacol. 2014 Jul;62(1):3-14. doi: 10.1016/j.vph.2014.04.006. Epub 2014 May 2. PubMed PMID: 24792192. 15: Liu L, Wu Y, Huang X. Orientin protects myocardial cells against hypoxia-reoxygenation injury through induction of autophagy. Eur J Pharmacol. 2016 Apr 5;776:90-8. doi: 10.1016/j.ejphar.2016.02.037. Epub 2016 Feb 11. PubMed PMID: 26875637. 16: Qi S, Feng Z, Li Q, Qi Z, Zhang Y. Inhibition of ROS-mediated activation Src-MAPK/AKT signaling by orientin alleviates H(2)O(2)-induced apoptosis in PC12 cells. Drug Des Devel Ther. 2018 Nov 16;12:3973-3984. doi: 10.2147/DDDT.S178217. eCollection 2018. PubMed PMID: 30510405; PubMed Central PMCID: PMC6248275. 17: Da Silva RZ, Yunes RA, de Souza MM, Delle Monache F, Cechinel-Filho V. Antinociceptive properties of conocarpan and orientin obtained from Piper solmsianum C. DC. var. solmsianum (Piperaceae). J Nat Med. 2010 Oct;64(4):402-8. doi: 10.1007/s11418-010-0421-x. Epub 2010 May 15. PubMed PMID: 20473574. 18: Kim SJ, Pham TH, Bak Y, Ryu HW, Oh SR, Yoon DY. Orientin inhibits invasion by suppressing MMP-9 and IL-8 expression via the PKCα/ ERK/AP-1/STAT3-mediated signaling pathways in TPA-treated MCF-7 breast cancer cells. Phytomedicine. 2018 Nov 15;50:35-42. doi: 10.1016/j.phymed.2018.09.172. Epub 2018 Sep 18. PubMed PMID: 30466990. 19: Chen F, Zhang Q, Liu J, Gu H, Yang L. An efficient approach for the extraction of orientin and vitexin from Trollius chinensis flowers using ultrasonic circulating technique. Ultrason Sonochem. 2017 Jul;37:267-278. doi: 10.1016/j.ultsonch.2017.01.012. Epub 2017 Jan 10. PubMed PMID: 28427633. 20: Li F, Zong J, Zhang H, Zhang P, Xu L, Liang K, Yang L, Yong H, Qian W. Orientin Reduces Myocardial Infarction Size via eNOS/NO Signaling and Thus Mitigates Adverse Cardiac Remodeling. Front Pharmacol. 2017 Dec 21;8:926. doi: 10.3389/fphar.2017.00926. eCollection 2017. PubMed PMID: 29311930; PubMed Central PMCID: PMC5742593.