異香草醛

異香草醛
	IUPAC名; 3-Hydroxy-4-methoxybenzaldehyde
別名	5-Formylguaiacol; 3-Hydroxy-p-anisaldehyde; 3-Hydroxy-4-methoxybenzaldehyde; Isovanilline
識別
CAS號	621-59-0
PubChem	12127
ChemSpider	11629
SMILES	COC1=CC=C(C=O)C=C1O;
Beilstein	1073021
EINECS	210-694-9
RTECS	CU6540000
MeSH	Isovanillin
性質
化學式	C8H8O3
摩爾質量	152.15 g·mol−1
外觀	半透明晶體
熔點	115 °C（388 K）
沸點	179 °C（452 K）（15 mmHg）; 135—145 °C（408—418 K）（0.02 Torr）
log P	1.25
pKa	9.248
危險性
警示術語	R：R36/37/38
安全術語	S：S26, S36/37
歐盟分類	Xi
相關物質
相關化學品	茴香醛; 丁香油酚; 苯酚; 香草醛
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

異香草醛（英語：Isovanillin；又稱異香蘭素）是一種酚醛，香草醛的同分異構體之一^[4]。它是醛氧化酶（英語：aldehyde oxidase）的一種選擇性抑制劑，能被醛脫氫酶（英語：aldehyde dehydrogenase）代謝成異香草酸（德語：Isovanillinsäure），這種特性使得異香草醛能夠用於酒精厭惡療法^[5]。異香草醛可以作為嗎啡全合成的前體^[6]^[7]。文獻中已有描述其（和香草醛）在大鼠體內可能的代謝過程^[8]^[9]。

參見

香草醛
2-羥基-5-甲氧基苯甲醛（英語：2-Hydroxy-5-methoxybenzaldehyde）
鄰香草醛
2-羥基-4-甲氧基苯甲醛

參考資料

^ Isovanillin. The PubChem Project. National Center for Biotechnology Information. [2021-04-20]. （原始內容存檔於2012-11-03）.
^ Angela M. Bernard, M. Rossella Ghiani, Pier Paolo Piras, Antonio Rivoldini. Dealkylation of Activated Alkyl Aryl Ethers Using Lithium Chloride in Dimethylformamide. Synthesis. 1989, 1989 (04): 287–289 [2021-04-21]. ISSN 0039-7881. doi:10.1055/s-1989-27225. （原始內容存檔於2018-06-03）（英語）.
^ Schwarz, R.; Capek, K. A new synthesis of homoisovanillic acid and of isovanillin. Monatshefte fuer Chemie, 1952. 83: 883-893. ISSN: 0026-9247.
^ isovanillin - Compound Summary (CID 12127). [2021-04-20]. （原始內容存檔於2013-12-27）.
^ Georgios Panoutsopoulos; Christine Beedham. Enzymatic Oxidation of Vanillin, Isovanillin and Protocatechuic Aldehyde with Freshly Prepared Guinea Pig Liver Slices. Cell Physiol Biochem. 2005, 15 (1–4): 89–98 [2021-04-20]. PMID 15665519. S2CID 17057295. arXiv:quant-ph/0403227 . doi:10.1159/000083641. （原始內容存檔於2011-06-15）.
^ Uchida, Kenji; Yokoshima, Satoshi; Kan, Toshiyuki; Fukuyama, Tohru. Total Synthesis of (±)-Morphine. Organic Letters. 2006, 8 (23): 5311–5313. PMID 17078705. doi:10.1021/ol062112m.
^ Uchida, Kenji; Yokoshima, Satoshi; Kan, Toshiyuki; Fukuyama, Tohru. Total Synthesis of (±)-Morphine. Heterocycles. 2009, 77 (2): 1219–1234 [27 December 2013]. PMID 17078705. doi:10.3987/COM-08-S(F)103.
^ Strand, L. P.; Scheline, R. R. The metabolism of vanillin and isovanillin in the rat. Xenobiotica; the Fate of Foreign Compounds in Biological Systems. January 1975, 5 (1): 49–63. ISSN 0049-8254. PMID 1154798. doi:10.3109/00498257509056093.
^ Vanillin and isovanillin metabolism. WikiPathways. 2019-10-31. （原始內容存檔於2021-04-20）.

[1] Isovanillin. The PubChem Project. National Center for Biotechnology Information. [2021-04-20]. （原始內容存檔於2012-11-03）.

[2] Angela M. Bernard, M. Rossella Ghiani, Pier Paolo Piras, Antonio Rivoldini. Dealkylation of Activated Alkyl Aryl Ethers Using Lithium Chloride in Dimethylformamide. Synthesis. 1989, 1989 (04): 287–289 [2021-04-21]. ISSN 0039-7881. doi:10.1055/s-1989-27225. （原始內容存檔於2018-06-03）（英語）.

[3] Schwarz, R.; Capek, K. A new synthesis of homoisovanillic acid and of isovanillin. Monatshefte fuer Chemie, 1952. 83: 883-893. ISSN: 0026-9247.

[4] sovanillin - Compound Summary (CID 12127). [2021-04-20]. （原始內容存檔於2013-12-27）.

[5] Georgios Panoutsopoulos; Christine Beedham. Enzymatic Oxidation of Vanillin, Isovanillin and Protocatechuic Aldehyde with Freshly Prepared Guinea Pig Liver Slices. Cell Physiol Biochem. 2005, 15 (1–4): 89–98 [2021-04-20]. PMID 15665519. S2CID 17057295. arXiv:quant-ph/0403227 . doi:10.1159/000083641. （原始內容存檔於2011-06-15）.

[6] Uchida, Kenji; Yokoshima, Satoshi; Kan, Toshiyuki; Fukuyama, Tohru. Total Synthesis of (±)-Morphine. Organic Letters. 2006, 8 (23): 5311–5313. PMID 17078705. doi:10.1021/ol062112m.

[7] Uchida, Kenji; Yokoshima, Satoshi; Kan, Toshiyuki; Fukuyama, Tohru. Total Synthesis of (±)-Morphine. Heterocycles. 2009, 77 (2): 1219–1234 [27 December 2013]. PMID 17078705. doi:10.3987/COM-08-S(F)103.

[8] Strand, L. P.; Scheline, R. R. The metabolism of vanillin and isovanillin in the rat. Xenobiotica; the Fate of Foreign Compounds in Biological Systems. January 1975, 5 (1): 49–63. ISSN 0049-8254. PMID 1154798. doi:10.3109/00498257509056093.

[9] Vanillin and isovanillin metabolism. WikiPathways. 2019-10-31. （原始內容存檔於2021-04-20）.

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