Luteolin | CAS#491-70-3

MedKoo Cat#: 326683 | Name: Luteolin

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Description:

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

Luteolin is a flavone, a type of flavonoid. Like all flavonoids, it has a yellow crystalline appearance. Luteolin belongs to a group of naturally occurring compounds called flavonoids that are found widely in the plant kingdom. Luteolin possesses many beneficial properties including antioxidant, anti- inflammatory, anti-bacterial, anti-diabetic and anti-proliferative actions.

Chemical Structure

Luteolin

CAS#491-70-3

Theoretical Analysis

MedKoo Cat#: 326683

Name: Luteolin

CAS#: 491-70-3

Chemical Formula: C15H10O6

Exact Mass: 286.0477

Molecular Weight: 286.24

Elemental Analysis: C, 62.94; H, 3.52; O, 33.54

Price and Availability

Size	Price	Availability
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 400.00	Ready to ship
5g	USD 650.00	2 Weeks

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Related CAS #

6113-16-2 (hydrate) 491-70-3

Synonym

BRN 0292084; C.I. 75590; C.I. Natural Yellow 2; CCRIS 3790; Cyanidenon 1470; Digitoflavone; Flacitran; Luteoline; Luteolol; Salifazide; Luteolin

IUPAC/Chemical Name

2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyrone

InChi Key

IQPNAANSBPBGFQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H

SMILES Code

O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=CC(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, not in water

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A22K03S23

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Luteolin (Luteoline) is a potent Nrf2 inhibitor.

In vitro activity:

The results demonstrated that TNF-α induced a significant increase in IL-1β (Fig. 2A) and IL-6 (Fig. 2B) levels, while luteolin treatment decreased the expression levels of these inflammatory factors in a concentration-dependent manner. Compared with the TNF-α group, luteolin decreased TNF-α-induced apoptosis in a concentration-dependent manner. To further verify this result, the expression levels of specific apoptosis-related proteins were examined by western blot analysis (Fig. 2D). The results demonstrated that TNF-α induction increased the expression levels of the pro-apoptotic proteins Bax and cleaved caspase 3, whereas it reduced the expression level of the anti-apoptotic protein Bcl-2. However, treatment of the cells with luteolin reversed these effects. Reference: Exp Ther Med. 2022 May 26;24(1):469. https://pubmed.ncbi.nlm.nih.gov/35747154/

In vivo activity:

Luteolin binds to PPARγ and reduced the infarct area in MCAO/R treated rats. The brain infarct area was observed using TTC staining (Fig. 1C) and the infarct area is shown in white. From Fig. 1C, this study found that 25 mg/kg/d luteolin and 50 mg/kg/d luteolin greatly reduced the infarct area when contrasted to the MCAO/R (vehicle) group. Reference: BMC Complement Med Ther. 2022 Jul 1;22(1):176. https://pubmed.ncbi.nlm.nih.gov/35778706/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	69.87
	DMF:PBS (pH 7.2) (1:5)	1.0	3.49
	DMSO	39.3	137.39
	Ethanol	5.0	17.47

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 286.24 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

Formulation protocol:

1. Guo T, Liu P, Wang Z, Zheng Y, Huang W, Kong D, Ding L, Lv Q, Wang Z, Jiang H, Jiang Y, Sun L. Luteolin Binds Streptolysin O Toxin and Inhibits Its Hemolytic Effects and Cytotoxicity. Front Pharmacol. 2022 Jul 7;13:942180. doi: 10.3389/fphar.2022.942180. PMID: 35873567; PMCID: PMC9300923. 2. Xie T, Yuan J, Mei L, Li P, Pan R. Luteolin suppresses TNF-α-induced inflammatory injury and senescence of nucleus pulposus cells via the Sirt6/NF-κB pathway. Exp Ther Med. 2022 May 26;24(1):469. doi: 10.3892/etm.2022.11396. PMID: 35747154; PMCID: PMC9204575. 3. Li L, Pan G, Fan R, Li D, Guo L, Ma L, Liang H, Qiu J. Luteolin alleviates inflammation and autophagy of hippocampus induced by cerebral ischemia/reperfusion by activating PPAR gamma in rats. BMC Complement Med Ther. 2022 Jul 1;22(1):176. doi: 10.1186/s12906-022-03652-8. PMID: 35778706; PMCID: PMC9248165. 4. Zhu Q, Meng P, Han Y, Yang H, Yang Q, Liu Z, Wang Y, Long M. Luteolin Induced Hippocampal Neuronal Pyroptosis Inhibition by Regulation of miR-124-3p/TNF-α/TRAF6 Axis in Mice Affected by Breast-Cancer-Related Depression. Evid Based Complement Alternat Med. 2022 May 6;2022:2715325. doi: 10.1155/2022/2715325. PMID: 35571739; PMCID: PMC9106465.

In vitro protocol:

In vivo protocol:

1. Li L, Pan G, Fan R, Li D, Guo L, Ma L, Liang H, Qiu J. Luteolin alleviates inflammation and autophagy of hippocampus induced by cerebral ischemia/reperfusion by activating PPAR gamma in rats. BMC Complement Med Ther. 2022 Jul 1;22(1):176. doi: 10.1186/s12906-022-03652-8. PMID: 35778706; PMCID: PMC9248165. 2. Zhu Q, Meng P, Han Y, Yang H, Yang Q, Liu Z, Wang Y, Long M. Luteolin Induced Hippocampal Neuronal Pyroptosis Inhibition by Regulation of miR-124-3p/TNF-α/TRAF6 Axis in Mice Affected by Breast-Cancer-Related Depression. Evid Based Complement Alternat Med. 2022 May 6;2022:2715325. doi: 10.1155/2022/2715325. PMID: 35571739; PMCID: PMC9106465.

1: Popov AM, Krivoshapko ON, Klimovich AA, Artyukov AA. [Biological activity and mechanisms of therapeutic action of rosmarinic acid, luteolin and its sulphated derivatives]. Biomed Khim. 2016 Jan-Feb;62(1):22-30. doi: 10.18097/PBMC20166201022. Review. Russian. PubMed PMID: 26973183. 2: Nabavi SF, Braidy N, Gortzi O, Sobarzo-Sanchez E, Daglia M, Skalicka-Woźniak K, Nabavi SM. Luteolin as an anti-inflammatory and neuroprotective agent: A brief review. Brain Res Bull. 2015 Oct;119(Pt A):1-11. doi: 10.1016/j.brainresbull.2015.09.002. Epub 2015 Sep 8. Review. PubMed PMID: 26361743. 3: Theoharides TC, Stewart JM, Hatziagelaki E, Kolaitis G. Brain "fog," inflammation and obesity: key aspects of neuropsychiatric disorders improved by luteolin. Front Neurosci. 2015 Jul 3;9:225. doi: 10.3389/fnins.2015.00225. eCollection 2015. Review. PubMed PMID: 26190965; PubMed Central PMCID: PMC4490655. 4: Pandurangan AK, Esa NM. Luteolin, a bioflavonoid inhibits colorectal cancer through modulation of multiple signaling pathways: a review. Asian Pac J Cancer Prev. 2014;15(14):5501-8. Review. PubMed PMID: 25081655. 5: Kritas SK, Saggini A, Varvara G, Murmura G, Caraffa A, Antinolfi P, Toniato E, Pantalone A, Neri G, Frydas S, Rosati M, Tei M, Speziali A, Saggini R, Pandolfi F, Cerulli G, Theoharides TC, Conti P. Luteolin inhibits mast cell-mediated allergic inflammation. J Biol Regul Homeost Agents. 2013 Oct-Dec;27(4):955-9. Review. PubMed PMID: 24382176. 6: Jiang D, Li D, Wu W. Inhibitory effects and mechanisms of luteolin on proliferation and migration of vascular smooth muscle cells. Nutrients. 2013 May 17;5(5):1648-59. doi: 10.3390/nu5051648. Review. PubMed PMID: 23686014; PubMed Central PMCID: PMC3708342. 7: Xu T, Li D, Jiang D. Targeting cell signaling and apoptotic pathways by luteolin: cardioprotective role in rat cardiomyocytes following ischemia/reperfusion. Nutrients. 2012 Dec 12;4(12):2008-19. doi: 10.3390/nu4122008. Review. PubMed PMID: 23235403; PubMed Central PMCID: PMC3546619. 8: López-Lázaro M. Distribution and biological activities of the flavonoid luteolin. Mini Rev Med Chem. 2009 Jan;9(1):31-59. Review. PubMed PMID: 19149659. 9: Lin Y, Shi R, Wang X, Shen HM. Luteolin, a flavonoid with potential for cancer prevention and therapy. Curr Cancer Drug Targets. 2008 Nov;8(7):634-46. Review. PubMed PMID: 18991571; PubMed Central PMCID: PMC2615542. 10: Seelinger G, Merfort I, Wölfle U, Schempp CM. Anti-carcinogenic effects of the flavonoid luteolin. Molecules. 2008 Oct 22;13(10):2628-51. Review. PubMed PMID: 18946424. 11: Seelinger G, Merfort I, Schempp CM. Anti-oxidant, anti-inflammatory and anti-allergic activities of luteolin. Planta Med. 2008 Nov;74(14):1667-77. doi: 10.1055/s-0028-1088314. Epub 2008 Oct 20. Review. PubMed PMID: 18937165. 12: Ying JY, Gu SJ, Yao TW. [Research progress on interactions between luteolin (glucosides) and drug-metabolizing enzyme]. Yao Xue Xue Bao. 2008 Apr;43(4):335-42. Review. Chinese. PubMed PMID: 18664192. 13: Theoharides TC, Kempuraj D, Iliopoulou BP. Mast cells, T cells, and inhibition by luteolin: implications for the pathogenesis and treatment of multiple sclerosis. Adv Exp Med Biol. 2007;601:423-30. Review. PubMed PMID: 17713031. 14: Zhang FF, Shen HM, Zhu XQ. [Research progress on anti-tumor effects of luteolin]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2006 Sep;35(5):573-8. Review. Chinese. PubMed PMID: 17063556.