丙二醛

丙二醛
	IUPAC名; propanedial
英文名	Malondialdehyde
識別
縮寫	MDA
CAS號	542-78-9
PubChem	10964
ChemSpider	10499
SMILES	O=CCC=O;
InChI	1/C3H4O2/c4-2-1-3-5/h2-3H,1H2;
InChIKey	WSMYVTOQOOLQHP-UHFFFAOYAU
KEGG	C19440
性質
化學式	C3H4O2
摩爾質量	72.06 g·mol−1
外觀	針狀固體
密度	0.991 g/mL
熔點	72 °C（345 K）
沸點	108 °C（381 K）
危險性
PEL	none
相關物質
相關烯醛	羥基丙二醛（英語：Glucic acid）; 4-羥基-2-壬烯醛
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

丙二醛，簡稱MDA，是一種有機化合物，化學式 CH₂(CHO)₂。它是一種無色液體，反應性極高，通常以烯醇式存在。^[2]

快速預覽 丙二醛, 識別 ...

關閉

Remove ads

丙二醛通常以烯醇式存在：^[2]

CH₂(CHO)₂ → HOC(H)=CH-CHO

在實驗室中，丙二醛可以由對應的縮醛1,1,3,3-四甲氧基丙烷水解而成。與丙二醛不同，這種縮醛是穩定，可商購的。^[2]

丙二醛可以由脂肪的脂質過氧化而成。^[3]它是血栓素A2的合成中的重要產物，其中環加氧酶1或環加氧酶2通過血小板和一系列其他細胞和組織，將花生四烯酸代謝成前列腺素H2。前列腺素H2再被血栓烷合成酶（英語：Thromboxane-A synthase）進一步代謝為血栓素A2、12-羥基十七碳三烯酸（英語：12-Hydroxyheptadecatrienoic acid）和丙二醛。^[4]^[5]

活性氧類會降解脂肪，形成丙二醛。^[6]這種醛具有高反應性，是許多反應性親電試劑之一，可在細胞中引起毒性應激並形成稱為高級脂肪氧化終產物 (ALE) 的共價蛋白質加合物，類似於高級糖化終產物(AGE)。^[7]這種醛的產生可用來測量生物的氧化應激水平。^[8]^[9]

丙二醛會和DNA中的脫氧腺苷和脫氧鳥苷反應，形成DNA加合物（英語：DNA adducts），主要會產生突變原M₁G（英語：M1G）。^[10]精氨酸的胍基會與丙二醛縮合，得到2-氨基嘧啶。

分析

丙二醛和其它硫代巴比妥酸反應性物質（英語：TBARS） (TBARS) 會與兩倍的硫代巴比妥酸（英語：thiobarbituric acid）縮合，生成可通過分光光度法測定的螢光紅色衍生物。^[2]^[11] 1-甲基-2-苯基吲哚是另一種更具選擇性的試劑。^[2]

丙二醛具有高反應性，有潛在的致突變性。^[12] 它被發現存在於加熱的食用油中，例如向日葵油和棕櫚油。^[13]

根據一項研究，患有圓錐角膜和大疱性角膜病變（英語：Bullous keratopathy）的患者的角膜中，丙二醛的水平升高了。^[14]丙二醛也可以在骨關節炎患者的關節組織切片中找到。^[15]

在評估精子中的膜損傷時，也可以考慮丙二醛的水平（脂質過氧化的標誌）。這是至關重要的，因為氧化應激通過改變膜流動性、滲透性和損害精子功能來影響精子功能。^[16]

[1]
NIOSH Pocket Guide to Chemical Hazards. #0377. NIOSH.
[2]
V. Nair, C. L. O'Neil, P. G. Wang "Malondialdehyde", Encyclopedia of Reagents for Organic Synthesis, 2008, John Wiley & Sons, New York. doi:10.1002/047084289X.rm013.pub2 Article Online Posting Date: March 14, 2008
[3]
Davey MW1, Stals E, Panis B, Keulemans J, Swennen RL. High-throughput determination of malondialdehyde in plant tissues. Analytical Biochemistry. 2005, 347 (2): 201–207. PMID 16289006. doi:10.1016/j.ab.2005.09.041.
[4]
J. Biol. Chem. 248:5673; 1973
[5]
Proc. Natl. Acad. Sci. USA 71:3400; 1974
[6]
Pryor WA, Stanley JP. Letter: A suggested mechanism for the production of malondialdehyde during the autoxidation of polyunsaturated fatty acids. Nonenzymatic production of prostaglandin endoperoxides during autoxidation. J. Org. Chem. 1975, 40 (24): 3615–7. PMID 1185332. doi:10.1021/jo00912a038.
[7]
Farmer EE, Davoine C. Reactive electrophile species. Curr. Opin. Plant Biol. 2007, 10 (4): 380–6. PMID 17646124. doi:10.1016/j.pbi.2007.04.019.
[8]
Moore K, Roberts LJ. Measurement of lipid peroxidation. Free Radic. Res. 1998, 28 (6): 659–71. PMID 9736317. doi:10.3109/10715769809065821.
[9]
Del Rio D, Stewart AJ, Pellegrini N. A review of recent studies on malondialdehyde as toxic molecule and biological marker of oxidative stress. Nutr Metab Cardiovasc Dis. 2005, 15 (4): 316–28. PMID 16054557. doi:10.1016/j.numecd.2005.05.003.
[10]
Marnett LJ. Lipid peroxidation-DNA damage by malondialdehyde. Mutat. Res. 1999, 424 (1–2): 83–95. PMID 10064852. doi:10.1016/S0027-5107(99)00010-X.
[11]
http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33 網際網路檔案館的存檔，存檔日期September 14, 2006，.
[12]
Hartman PE, Putative mutagens and carcinogens in foods. IV. Malonaldehyde (malondialdehyde) Environ Mutagen. 1983;5(4):603-7
[13]
Dourerdjou, P.; Koner, B. C. (2008), Effect of Different Cooking Vessels on Heat-Induced Lipid Peroxidation of Different Edible Oils" Journal of Food Biochemistry, 32: 740–751. doi:10.1111/j.1745-4514.2008.00195.x
[14]
Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ. Evidence of oxidative stress in human corneal diseases. J. Histochem. Cytochem. March 2002, 50 (3): 341–51. PMID 11850437. doi:10.1177/002215540205000306 .^{[永久失效連結]}
[15]
Tiku ML, Narla H, Jain M, Yalamanchili P. Glucosamine prevents in vitro collagen degradation in chondrocytes by inhibiting advanced lipoxidation reactions and protein oxidation. Arthritis Research & Therapy. 2007, 9 (4): R76. PMC 2206377 . PMID 17686167. doi:10.1186/ar2274.
[16]
Collodel, G.; Moretti, E.; Micheli, L.; Menchiari, A.; Moltoni, L.; Cerretani, D. Semen characteristics and malondialdehyde levels in men with different reproductive problems. Andrology. March 2015, 3 (2): 280–286. PMID 25331426. S2CID 28027300. doi:10.1111/andr.297 （英語）.

Remove ads

[PGCH-1] [1]
NIOSH Pocket Guide to Chemical Hazards. #0377. NIOSH.

[eEROS-2] [2]
V. Nair, C. L. O'Neil, P. G. Wang "Malondialdehyde", Encyclopedia of Reagents for Organic Synthesis, 2008, John Wiley & Sons, New York. doi:10.1002/047084289X.rm013.pub2 Article Online Posting Date: March 14, 2008

[pmid16289006-3] [3]
Davey MW1, Stals E, Panis B, Keulemans J, Swennen RL. High-throughput determination of malondialdehyde in plant tissues. Analytical Biochemistry. 2005, 347 (2): 201–207. PMID 16289006. doi:10.1016/j.ab.2005.09.041.

[4] [4]
J. Biol. Chem. 248:5673; 1973

[5] [5]
Proc. Natl. Acad. Sci. USA 71:3400; 1974

[6] [6]
Pryor WA, Stanley JP. Letter: A suggested mechanism for the production of malondialdehyde during the autoxidation of polyunsaturated fatty acids. Nonenzymatic production of prostaglandin endoperoxides during autoxidation. J. Org. Chem. 1975, 40 (24): 3615–7. PMID 1185332. doi:10.1021/jo00912a038.

[7] [7]
Farmer EE, Davoine C. Reactive electrophile species. Curr. Opin. Plant Biol. 2007, 10 (4): 380–6. PMID 17646124. doi:10.1016/j.pbi.2007.04.019.

[8] [8]
Moore K, Roberts LJ. Measurement of lipid peroxidation. Free Radic. Res. 1998, 28 (6): 659–71. PMID 9736317. doi:10.3109/10715769809065821.

[9] [9]
Del Rio D, Stewart AJ, Pellegrini N. A review of recent studies on malondialdehyde as toxic molecule and biological marker of oxidative stress. Nutr Metab Cardiovasc Dis. 2005, 15 (4): 316–28. PMID 16054557. doi:10.1016/j.numecd.2005.05.003.

[martnett-10] [10]
Marnett LJ. Lipid peroxidation-DNA damage by malondialdehyde. Mutat. Res. 1999, 424 (1–2): 83–95. PMID 10064852. doi:10.1016/S0027-5107(99)00010-X.

[11] [11]
http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33 網際網路檔案館的存檔，存檔日期September 14, 2006，.

[12] [12]
Hartman PE, Putative mutagens and carcinogens in foods. IV. Malonaldehyde (malondialdehyde) Environ Mutagen. 1983;5(4):603-7

[13] [13]
Dourerdjou, P.; Koner, B. C. (2008), Effect of Different Cooking Vessels on Heat-Induced Lipid Peroxidation of Different Edible Oils" Journal of Food Biochemistry, 32: 740–751. doi:10.1111/j.1745-4514.2008.00195.x

[pmid11850437-14] [14]
Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ. Evidence of oxidative stress in human corneal diseases. J. Histochem. Cytochem. March 2002, 50 (3): 341–51. PMID 11850437. doi:10.1177/002215540205000306 .^{[永久失效連結]}

[pmid17686167-15] [15]
Tiku ML, Narla H, Jain M, Yalamanchili P. Glucosamine prevents in vitro collagen degradation in chondrocytes by inhibiting advanced lipoxidation reactions and protein oxidation. Arthritis Research & Therapy. 2007, 9 (4): R76. PMC 2206377 . PMID 17686167. doi:10.1186/ar2274.

[16] [16]
Collodel, G.; Moretti, E.; Micheli, L.; Menchiari, A.; Moltoni, L.; Cerretani, D. Semen characteristics and malondialdehyde levels in men with different reproductive problems. Andrology. March 2015, 3 (2): 280–286. PMID 25331426. S2CID 28027300. doi:10.1111/andr.297 （英語）.

[2]

[1]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]

[16]

丙二醛

分析

Wikiwand in your browser!

丙二醛

分析

Wikiwand in your browser!

結構和製備

生物合成和反應性

危險性和病理學

參見

參考資料