4-hydroxynonenal
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MedKoo CAT#: 556019

CAS#: 75899-68-2

Description: 4-hydroxynonenal is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids. 4-hydroxy Nonenal is widely used as a marker of lipid peroxidation. 4-Hydroxynonenal Contributes to Fibroblast Senescence in Skin Photoaging Evoked by UV-A Radiation. 4-Hydroxynonenal induces Cx46 hemichannel inhibition through its carbonylation.


Chemical Structure

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4-hydroxynonenal
CAS# 75899-68-2

Theoretical Analysis

MedKoo Cat#: 556019
Name: 4-hydroxynonenal
CAS#: 75899-68-2
Chemical Formula: C9H16O2
Exact Mass: 156.115
Molecular Weight: 156.225
Elemental Analysis: C, 69.19; H, 10.32; O, 20.48

Price and Availability

Size Price Availability Quantity
200.0mg USD 1650.0 2 Weeks
500.0mg USD 2950.0 2 Weeks
1.0g USD 4850.0 2 Weeks
2.0g USD 7650.0 2 Weeks
5.0g USD 14950.0 2 Weeks
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Synonym: 4-hydroxy Nonenal; 4-hydroxynonenal;

IUPAC/Chemical Name: 4-hydroxy-2E-nonenal

InChi Key: InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+

InChi Code: InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+

SMILES Code: CCCCCC(O)/C=C/C=O

Appearance: Liquid

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

Product Data:

Biological target: Na+, K+-ATPase activity, Target IC50: 120 µM against Na+, K+-ATPase activity
In vitro activity: By using ferroptosis inhibitor ferrostatin-1 and measurement of ferroptotic cell death phenotype in both in vivo and in vitro cisplatin induced AKI model, the decreased blood urea nitrogen, creatinine, and tissue injury by ferrostatin-1 were observed, hence validated the essential involvement of ferroptosis in cisplatin induced AKI. VDR agonist paricalcitol could both functionally and histologically attenuate cisplatin induced AKI by decreasing lipid peroxidation (featured phenotype of ferroptosis), biomarker 4-hydroxynonenal (4HNE), and malondialdehyde (MDA), while reversing glutathione peroxidase 4 (GPX4, key regulator of ferroptosis) downregulation. VDR knockout mouse exhibited much more ferroptotic cell death and worsen kidney injury than wild type mice. And VDR deficiency remarkably decreased the expression of GPX4 under cisplatin stress in both in vivo and in vitro, further luciferase reporter gene assay showed that GPX4 were target gene of transcription factor VDR. In addition, in vitro study showed that GPX4 inhibition by siRNA largely abolished the protective effect of paricalcitol against cisplatin induced tubular cell injury. Besides, pretreatment of paricalcitol could also alleviated Erastin (an inducer of ferroptosis) induced cell death in HK-2 cell. These data suggested that ferroptosis plays an important role in cisplatin induced AKI. VDR activation can protect against cisplatin induced renal injury by inhibiting ferroptosis partly via trans-regulation of GPX4. Reference: Hu Z, Zhang H, Yi B, Yang S, Liu J, Hu J, Wang J, Cao K, Zhang W. VDR activation attenuate cisplatin induced AKI by inhibiting ferroptosis. Cell Death Dis. 2020 Jan 29;11(1):73. doi: 10.1038/s41419-020-2256-z. PMID: 31996668; PMCID: PMC6989512.
In vivo activity: Aldh3a1-/- zebrafish larvae displayed retinal vasodilatory alterations, impaired glucose homeostasis, which can be aggravated via pdx1 silencing induced hyperglycaemia. Unexpectedly, MG was not altered, but 4-hydroxynonenal (4-HNE), another prominent lipid peroxidation RCS exhibited high affinity with Aldh3a1, was increased in aldh3a1 mutants. 4-HNE was responsible for the retinal phenotype via pancreas disruption induced hyperglycaemia and can be rescued via l-Carnosine treatment. Furthermore, in type 2 diabetic patients, serum 4-HNE was increased and correlated with disease progression. Thus, our data suggest impaired 4-HNE detoxification and elevated 4-HNE concentration as biomarkers but also the possible inducers for diabetes, from genetic susceptibility to the pathological progression. Reference: Lou B, Boger M, Bennewitz K, Sticht C, Kopf S, Morgenstern J, Fleming T, Hell R, Yuan Z, Nawroth PP, Kroll J. Elevated 4-hydroxynonenal induces hyperglycaemia via Aldh3a1 loss in zebrafish and associates with diabetes progression in humans. Redox Biol. 2020 Oct;37:101723. doi: 10.1016/j.redox.2020.101723. Epub 2020 Sep 16. PMID: 32980661; PMCID: PMC7519378.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.0 320.04
DMF 0.0 320.04
Ethanol 0.0 320.04
PBS pH 7.2 0.0 6.4

Preparing Stock Solutions

The following data is based on the product molecular weight 156.225 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
Formulation protocol: Hu Z, Zhang H, Yi B, Yang S, Liu J, Hu J, Wang J, Cao K, Zhang W. VDR activation attenuate cisplatin induced AKI by inhibiting ferroptosis. Cell Death Dis. 2020 Jan 29;11(1):73. doi: 10.1038/s41419-020-2256-z. PMID: 31996668; PMCID: PMC6989512.
In vitro protocol: Hu Z, Zhang H, Yi B, Yang S, Liu J, Hu J, Wang J, Cao K, Zhang W. VDR activation attenuate cisplatin induced AKI by inhibiting ferroptosis. Cell Death Dis. 2020 Jan 29;11(1):73. doi: 10.1038/s41419-020-2256-z. PMID: 31996668; PMCID: PMC6989512.
In vivo protocol: Lou B, Boger M, Bennewitz K, Sticht C, Kopf S, Morgenstern J, Fleming T, Hell R, Yuan Z, Nawroth PP, Kroll J. Elevated 4-hydroxynonenal induces hyperglycaemia via Aldh3a1 loss in zebrafish and associates with diabetes progression in humans. Redox Biol. 2020 Oct;37:101723. doi: 10.1016/j.redox.2020.101723. Epub 2020 Sep 16. PMID: 32980661; PMCID: PMC7519378.

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1: Schröter A, Mahler HC, Sayed NB, Koulov AV, Huwyler J, Jahn M. 4-Hydroxynonenal - A Toxic Leachable from Clinically Used Administration Materials. J Pharm Sci. 2021 Jun 4:S0022-3549(21)00279-3. doi: 10.1016/j.xphs.2021.05.014. Epub ahead of print. PMID: 34090902.

2: Swiader A, Camaré C, Guerby P, Salvayre R, Negre-Salvayre A. 4-Hydroxynonenal Contributes to Fibroblast Senescence in Skin Photoaging Evoked by UV-A Radiation. Antioxidants (Basel). 2021 Feb 28;10(3):365. doi: 10.3390/antiox10030365. PMID: 33670907; PMCID: PMC7997366.

3: Sunjic SB, Gasparovic AC, Jaganjac M, Rechberger G, Meinitzer A, Grune T, Kohlwein SD, Mihaljevic B, Zarkovic N. Sensitivity of Osteosarcoma Cells to Concentration-Dependent Bioactivities of Lipid Peroxidation Product 4-Hydroxynonenal Depend on Their Level of Differentiation. Cells. 2021 Jan 29;10(2):269. doi: 10.3390/cells10020269. PMID: 33572933; PMCID: PMC7912392.

4: Schröter A, Koulov AV, Huwyler J, Mahler HC, Jahn M. 4-Hydroxynonenal is An Oxidative Degradation Product of Polysorbate 80. J Pharm Sci. 2021 Jun;110(6):2524-2530. doi: 10.1016/j.xphs.2021.01.027. Epub 2021 Feb 2. PMID: 33545186.

5: Keller J, Chevolleau S, Noguer-Meireles MH, Pujos-Guillot E, Delosière M, Chantelauze C, Joly C, Blas-Y-Estrada F, Jouanin I, Durand D, Pierre F, Debrauwer L, Theodorou V, Guéraud F. Heme-Iron-Induced Production of 4-Hydroxynonenal in Intestinal Lumen May Have Extra-Intestinal Consequences through Protein-Adduct Formation. Antioxidants (Basel). 2020 Dec 17;9(12):1293. doi: 10.3390/antiox9121293. PMID: 33348697; PMCID: PMC7766870.

6: Chiang YF, Chen HY, Chang YJ, Shih YH, Shieh TM, Wang KL, Hsia SM. Protective Effects of Fucoxanthin on High Glucose- and 4-Hydroxynonenal (4-HNE)-Induced Injury in Human Retinal Pigment Epithelial Cells. Antioxidants (Basel). 2020 Nov 25;9(12):1176. doi: 10.3390/antiox9121176. PMID: 33255669; PMCID: PMC7760030.

7: Na-Ek P, Punsawad C. Expression of 4-Hydroxynonenal (4-HNE) and Heme Oxygenase-1 (HO-1) in the Kidneys of Plasmodium berghei-Infected Mice. J Trop Med. 2020 Oct 23;2020:8813654. doi: 10.1155/2020/8813654. PMID: 33149743; PMCID: PMC7603615.

8: Geib T, Iacob C, Jribi R, Fernandes J, Benderdour M, Sleno L. Identification of 4-hydroxynonenal-modified proteins in human osteoarthritic chondrocytes. J Proteomics. 2021 Feb 10;232:104024. doi: 10.1016/j.jprot.2020.104024. Epub 2020 Oct 26. PMID: 33122130.

9: Siddiqui MA, Farshori NN, Al-Oqail MM, Pant AB, Al-Khedhairy AA. Neuroprotective Effects of Withania somnifera on 4-Hydroxynonenal Induced Cell Death in Human Neuroblastoma SH-SY5Y Cells Through ROS Inhibition and Apoptotic Mitochondrial Pathway. Neurochem Res. 2021 Feb;46(2):171-182. doi: 10.1007/s11064-020-03146-4. Epub 2020 Oct 14. PMID: 33052512.

10: Lou B, Boger M, Bennewitz K, Sticht C, Kopf S, Morgenstern J, Fleming T, Hell R, Yuan Z, Nawroth PP, Kroll J. Elevated 4-hydroxynonenal induces hyperglycaemia via Aldh3a1 loss in zebrafish and associates with diabetes progression in humans. Redox Biol. 2020 Oct;37:101723. doi: 10.1016/j.redox.2020.101723. Epub 2020 Sep 16. PMID: 32980661; PMCID: PMC7519378.

11: Shin SW, Kim DH, Jeon WK, Han JS. 4-Hydroxynonenal Immunoreactivity Is Increased in the Frontal Cortex of 5XFAD Transgenic Mice. Biomedicines. 2020 Sep 3;8(9):326. doi: 10.3390/biomedicines8090326. PMID: 32899155; PMCID: PMC7554765.

12: Gallo G, Sprovieri P, Martino G. 4-hydroxynonenal and oxidative stress in several organelles and its damaging effects on cell functions. J Physiol Pharmacol. 2020 Feb;71(1). doi: 10.26402/jpp.2020.1.07. Epub 2020 Jun 13. PMID: 32554842.

13: Liu H, Gambino F Jr, Algenio CS, Wu C, Gao Y, Bouchard CS, Qiao L, Bu P, Zhao S. Inflammation and oxidative stress induced by lipid peroxidation metabolite 4-hydroxynonenal in human corneal epithelial cells. Graefes Arch Clin Exp Ophthalmol. 2020 Aug;258(8):1717-1725. doi: 10.1007/s00417-020-04647-2. Epub 2020 May 22. PMID: 32445015.

14: Allegra M, Restivo I, Fucarino A, Pitruzzella A, Vasto S, Livrea MA, Tesoriere L, Attanzio A. Proeryptotic Activity of 4-Hydroxynonenal: A New Potential Physiopathological Role for Lipid Peroxidation Products. Biomolecules. 2020 May 16;10(5):770. doi: 10.3390/biom10050770. PMID: 32429353; PMCID: PMC7277761.

15: Retamal MA, Fiori MC, Fernandez-Olivares A, Linsambarth S, Peña F, Quintana D, Stehberg J, Altenberg GA. 4-Hydroxynonenal induces Cx46 hemichannel inhibition through its carbonylation. Biochim Biophys Acta Mol Cell Biol Lipids. 2020 Aug;1865(8):158705. doi: 10.1016/j.bbalip.2020.158705. Epub 2020 Mar 31. PMID: 32244060.

16: Oruc Y, Celik F, Ozgur G, Beyazyildiz E, Ugur K, Yardim M, Sahin I, Akkoc RF, Aydin S. ALTERED BLOOD AND AQUEOUS HUMOR LEVELS OF ASPROSIN, 4-HYDROXYNONENAL, AND 8-HYDROXY-DEOXYGUANOSINE IN PATIENTS WITH DIABETES MELLITUS AND CATARACT WITH AND WITHOUT DIABETIC RETINOPATHY. Retina. 2020 Dec;40(12):2410-2416. doi: 10.1097/IAE.0000000000002776. PMID: 32091490.

17: Kendal Netherton J, Hetherington L, Anne Ogle R, Mazloumi Gavgani M, Velkov T, Izabel Bilbin Villaverde A, Tanphaichitr N, Andrew Baker M. Mass Spectrometry Reveals New Insights into the Production of Superoxide Anions and 4-Hydroxynonenal Adducted Proteins in Human Sperm. Proteomics. 2020 Feb;20(3-4):e2070024. doi: 10.1002/pmic.202070024. Erratum for: Proteomics. 2020 Jan;20(2):e1900205. PMID: 32073236.

18: Petkovic I, Bresgen N, Gilardoni E, Regazzoni L, Uchida K, Aldini G, Siems W, Eckl P. In Vitro Aging of Human Skin Fibroblasts: Age-Dependent Changes in 4-Hydroxynonenal Metabolism. Antioxidants (Basel). 2020 Feb 11;9(2):150. doi: 10.3390/antiox9020150. PMID: 32053996; PMCID: PMC7070748.

19: Guo J, Wang J, Guo Y, Feng J. Association of aspirin resistance with 4-hydroxynonenal and its impact on recurrent cerebral infarction in patients with acute cerebral infarction. Brain Behav. 2020 Mar;10(3):e01562. doi: 10.1002/brb3.1562. Epub 2020 Feb 6. PMID: 32027781; PMCID: PMC7066347.

20: Netherton JK, Hetherington L, Ogle RA, Gavgani MM, Velkov T, Villaverde AIB, Tanphaichitr N, Baker MA. Mass Spectrometry Reveals New Insights into the Production of Superoxide Anions and 4-Hydroxynonenal Adducted Proteins in Human Sperm. Proteomics. 2020 Jan;20(2):e1900205. doi: 10.1002/pmic.201900205. Epub 2020 Jan 9. Erratum in: Proteomics. 2020 Feb;20(3-4):e2070024. PMID: 31846556.