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870608 | 4-HNE-dimethylacetal

(E)-4R-hydroxynonenal-dimethylacetal (Each vial contains 6.8mg which yields ~5.2mg 4-HNE after deprotection)

4-HNE-dimethylacetal

Hexane

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5mg 870608H-5mg 870608H-5mg $204.40
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4-HNE-dimethylacetal

(E)-4R-hydroxynonenal-dimethylacetal (Each vial contains 6.8mg which yields ~5.2mg 4-HNE after deprotection)

4-Hydroxynonenal (4-HNE or HNE) is an α,β-unsaturated hydroxyalkenal which is produced by lipid peroxidation in cells. 4-HNE has been hypothesized by several researchers to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular adhesion.
The dimethylacetal derivative is a more stable form of 4-HNE which is good for long term storage of the compound during use. It can be easily converted to 4-HNE in the presence of acid (see deprotection procedure).
Each vial contains 6.8mg which yields ~5.2mg 4-HNE after deprotection.
Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C11H22O3
Percent Composition
C 65.31%, H 10.96%, O 23.73%
Purity
>95% Each vial contains 6.8mg which yields ~5.2mg 4-HNE after deprotection.
Stability
1 Year
Storage Temperature
-20°C
CAS Number
119009-01-7
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
202.291
Exact Mass
202.157
Synonyms
4R-HNE-DA
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References

Chen CH, Budas GR, Churchill EN, Disatnik MH, Hurley TD, Mochly-Rosen D. Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart. Science. 2008 Sep 12;321(5895):1493-5. doi: 10.1126/science.1158554. PMID: 18787169; PMCID: PMC2741612.

 PubMed ID: 18787169

Awasthi YC, Yang Y, Tiwari NK, Patrick B, Sharma A, Li J, Awasthi S. Regulation of 4-hydroxynonenal-mediated signaling by glutathione S-transferases. Free Radic Biol Med. 2004 Sep 1;37(5):607-19. doi: 10.1016/j.freeradbiomed.2004.05.033. PMID: 15288119.

 PubMed ID: 15288119

Sharma R, Brown D, Awasthi S, Yang Y, Sharma A, Patrick B, Saini MK, Singh SP, Zimniak P, Singh SV, Awasthi YC. Transfection with 4-hydroxynonenal-metabolizing glutathione S-transferase isozymes leads to phenotypic transformation and immortalization of adherent cells. Eur J Biochem. 2004 May;271(9):1690-701. doi: 10.1111/j.1432-1033.2004.04067.x. PMID: 15096208.

 PubMed ID: 15096208

Zarkovic N. 4-hydroxynonenal as a bioactive marker of pathophysiological processes. Mol Aspects Med. 2003 Aug-Oct;24(4-5):281-91. doi: 10.1016/s0098-2997(03)00023-2. PMID: 12893006.

 PubMed ID: 12893006

Zarkovic K. 4-hydroxynonenal and neurodegenerative diseases. Mol Aspects Med. 2003 Aug-Oct;24(4-5):293-303. doi: 10.1016/s0098-2997(03)00024-4. PMID: 12893007.

 PubMed ID: 12893007

Zarković N, Zarković K, Schaur RJ, Stolc S, Schlag G, Redl H, Waeg G, Borović S, Loncarić I, Jurić G, Hlavka V. 4-Hydroxynonenal as a second messenger of free radicals and growth modifying factor. Life Sci. 1999;65(18-19):1901-4. doi: 10.1016/s0024-3205(99)00444-0. PMID: 10576434.

 PubMed ID: 10576434

Esterbauer H, Schaur RJ, Zollner H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic Biol Med. 1991;11(1):81-128. doi: 10.1016/0891-5849(91)90192-6. PMID: 1937131.

 PubMed ID: 1937131
Deprotection Procedure
(1) Open glass ampoule and transfer the contents of the ampoule to the Teflon vial (included) using a glass pipet or syringe. DO NOT USE PLASTIC.
(2) Evaporate the hexane under a gentle stream of nitrogen at room temperature. Keep lipid residue at 4°C for deprotection procedure.
(3) Add 1ml of 1mM HCl (4°C) and stir for about 45 minutes or close the vial and shake for 30 minutes.
(4) The suspension is initially cloudy and will become almost clear as deprotection occurs.
(5) The resulting aqueous HNE solution has a pH of 3 and contains ~5.2mg of aldehyde.
(6) This solution, if kept at 4°C, is stable for at least 24 hours.
(7) If neutralized (see note below), this product is stable for 6 hours.
(8) Once deprotected, we recommend that HNE be used immediately.
Note: HNE decomposes (polymerizes) in basic solution within a few minutes. Never use alkalies to neutralize the pH, but rather appropriately concentrated buffers. During saponification, methanol is generated. If methanol is undesirable, HNE can be extracted in chloroform or dichloromethane. HNE is only sparingly soluble in water.
Certificates of Analysis

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