异香草醛

异香草醛
	IUPAC名; 3-Hydroxy-4-methoxybenzaldehyde
别名	5-Formylguaiacol; 3-Hydroxy-p-anisaldehyde; 3-Hydroxy-4-methoxybenzaldehyde; Isovanilline
识别
CAS号	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
性质
化学式	C8H8O3
摩尔质量	152.15 g·mol−1
外观	半透明晶体
熔点	115 °C（388 K）
沸点	179 °C（452 K）（15 mmHg）; 135—145 °C（408—418 K）（0.02 Torr）
log P	1.25
pKa	9.248
危险性
警示术语	R：R36/37/38
安全术语	S：S26, S36/37
欧盟分类	Xi
相关物质
相关化学品	茴香醛; 丁香油酚; 苯酚; 香草醛
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

异香草醛（英语：Isovanillin；又称异香兰素）是一种酚醛，香草醛的同分异构体之一^[4]。它是醛氧化酶（英语：aldehyde oxidase）的一种选择性抑制剂，能被醛脱氢酶（英语：aldehyde dehydrogenase）代谢成异香草酸（德语：Isovanillinsäure），这种特性使得异香草醛能够用于酒精厌恶疗法^[5]。异香草醛可以作为吗啡全合成的前体^[6]^[7]。文献中已有描述其（和香草醛）在大鼠体内可能的代谢过程^[8]^[9]。

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参见

香草醛
2-羟基-5-甲氧基苯甲醛（英语：2-Hydroxy-5-methoxybenzaldehyde）
邻香草醛
2-羟基-4-甲氧基苯甲醛

参考资料

[1]
Isovanillin. The PubChem Project. National Center for Biotechnology Information. [2021-04-20]. （原始内容存档于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. （原始内容存档于2018-06-03）（英语）.
[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]
isovanillin - Compound Summary (CID 12127). [2021-04-20]. （原始内容存档于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. （原始内容存档于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. （原始内容存档于2021-04-20）.

[1] [1]
Isovanillin. The PubChem Project. National Center for Biotechnology Information. [2021-04-20]. （原始内容存档于2012-11-03）.

[2] [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. （原始内容存档于2018-06-03）（英语）.

[3] [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] [4]
isovanillin - Compound Summary (CID 12127). [2021-04-20]. （原始内容存档于2013-12-27）.

[5] [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. （原始内容存档于2011-06-15）.

[6] [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] [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] [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] [9]
Vanillin and isovanillin metabolism. WikiPathways. 2019-10-31. （原始内容存档于2021-04-20）.

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[6]

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