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香草醛

香草醛用途

Vanillin 是从香草豆中提取的单个分子,也是在香水,食品和药物中广泛使用的气味。

香草醛名称

[ CAS 号 ]:
121-33-5

[ 中文名 ]:
香草醛

[ 英文名 ]:
Vanillin

[中文别名 ]:

[英文别名 ]:

4-Hydroxy-3-methoxybenzaldehyde,Vanillic aldehyde
Lioxin
3-Methoxy-4-hydroxybenzaldehyde
Vanillin (contains H2SO4) Ethanol
VANILLA
VANILLINE
Zimco
4-oxy-3-methoxybenzaldehyde
Reference source: Negwer
Vinillin

香草醛生物活性

[ 描述 ]:

Vanillin 是从香草豆中提取的单个分子,也是在香水,食品和药物中广泛使用的气味。

[ 相关类别 ]:

研究领域 >> 其他

天然产物 >> 酸和醛

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

香草醛以剂量依赖性方式恢复UVA诱导的增殖减少。香草醛在测试浓度下没有凋亡作用。此外,UVA照射引起的OCT4,NANOG和SOX2的表达水平降低均由香草醛处理增加,表明香草醛减弱了UVA照射对hAMSCs的影响。基于荧光素酶报告基因测定,香草醛增加由UVA照射引起的HRE-荧光素酶报告基因的降低的活性。此外,用香草醛治疗减弱了由UVA照射引起的HIF-1α的减少的表达。结果显示,与UVA照射的对照相比,用香草醛处理hAMSCs导致PGE2和cAMP的产生显着降低[1]。

[体内研究]

抗抑郁治疗4周后,应激+香兰素和应激+氟西汀组的不动时间明显减少[F(4,42)= 34.73,P <0.01; F(4,42)= 13.55,P <0.01,分别为]。香草醛或氟西汀治疗显着减轻了CUMS模型动物蔗糖消耗的减少[F(4,42)= 12.32,P <0.01; F(4,42)= 5.65,P <0.01,分别为]。在CUMS模型大鼠中,与应激组相比,应激+香草醛和应激+氟西汀组的5-HT水平显着增加[F(4,42)= 4.846,P = 0.030;分别为F(4,42)= 4.846,P = 0.036,而两组中的去甲肾上腺素(NE)升高但不显着[F(4,42)= 6.977,ns]。与应激组相比,应激+香兰素组多巴胺(DA)也显着增加[F(4.42)= 6.174,P = 0.041] [2]。

[激酶实验]

用指定剂量的UVA照射hAMSC，然后在无血清条件下与指定浓度的香草醛一起温育3天。温育后，使用ELISA试剂盒测量培养上清液中PGE2或cAMP的浓度。将培养上清液加入96孔板中。将碱性磷酸酶缀合的PGE2或cAMP和针对PGE2或cAMP的抗体加入到样品孔中，并在室温下孵育2小时。然后用PBS洗涤样品孔并加入对硝基苯基磷酸盐（pNpp）底物溶液。最后，将样品在室温下孵育1小时，并根据制造商的说明书读取它们的吸光度值[1]。

[细胞实验]

用指定剂量的UVA照射hAMSC，然后在无血清条件下（在不含血清的DMEM中，在37℃，5％CO 2下）与1至100μM香草醛一起温育3天。三天后，使用BrdU掺入测定[1]测量细胞增殖。

[动物实验]

在该研究中使用雄性Sprague-Dawley大鼠（200至250g）。将动物分成三组，每组8至10只大鼠：应激+氟西汀组;压力+香兰素芳香疗法组和压力（未治疗）组。对于应激+氟西汀组，每天早晨给动物施用SSRI氟西汀的每日口服剂量（10mg / kg /天，在蒸馏水中稀释）。对于应力+香草醛组和球形切除术+香草醛组，香草醛在50cm高，35cm直径的有机玻璃圆筒中施用，其中两层由多孔树脂玻璃板隔开。将仍在其笼中的大鼠轻轻放置在上层上，并将5mL 600mg / L香草醛（在蒸馏水中）喷洒到下层的底部。应激组和对照组的大鼠接受与应激+香兰素组类似的处理，但没有任何气味给药[2]。

[参考文献]

[1]. Lee SY, et al. Vanillin attenuates negative effects of ultraviolet A on the stemness of human adipose tissue-derived mesenchymal stem cells. Food Chem Toxicol. 2016 Oct;96:62-9.

[2]. Xu J, et al. Vanillin-induced amelioration of depression-like behaviors in rats by modulating monoamine neurotransmitters in the brain. Psychiatry Res. 2015 Feb 28;225(3):509-14.

[相关活性小分子]

香草醛物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
282.6±20.0 °C at 760 mmHg

[ 熔点 ]:
81-83 °C(lit.)

[ 分子式 ]:
C₈H₈O₃

[ 分子量 ]:
152.147

[ 闪点 ]:
117.6±15.3 °C

[ 精确质量 ]:
152.047348

[ PSA ]:
46.53000

[ LogP ]:
1.19

[ 外观性状 ]:
白色或非常略黄色针状

[ 蒸汽密度 ]:
5.3 (vs air)

[ 蒸汽压 ]:
0.0±0.6 mmHg at 25°C

[ 折射率 ]:
1.588

[ 储存条件 ]:
Refrigerator

[ 稳定性 ]:
Stable. May discolour on exposure to light. Moisture-sensitive. Incompatible with strong oxidizing agents, perchloric acid.

[ 水溶解性 ]:
10 g/L (25 ºC)

香草醛MSDS

详细MSDS(安全技术说明书)

香草醛毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YW5775000

CHEMICAL NAME :: Vanillin

CAS REGISTRY NUMBER :: 121-33-5

BEILSTEIN REFERENCE NO. :: 0472792

LAST UPDATED :: 199710

DATA ITEMS CITED :: 24

MOLECULAR FORMULA :: C8-H8-O3

MOLECULAR WEIGHT :: 152.16

WISWESSER LINE NOTATION :: VHR DQ CO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1580 mg/kg

TOXIC EFFECTS :: Behavioral - coma

TYPE OF TEST :: LC - Lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >41700 ug/kg/4H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Liver - jaundice, other or unclassified

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1160 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - miosis (pupillary constriction) Behavioral - muscle weakness Lungs, Thorax, or Respiration - respiratory stimulation

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3925 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - coma

TYPE OF TEST :: LC - Lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >41700 ug/kg/2H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 475 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1320 mg/kg

TOXIC EFFECTS :: Vascular - BP lowering not characterized in autonomic section Vascular - acute arterial occlusion Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5010 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal) Gastrointestinal - peritonitis

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1400 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4480 mg/kg/70D-I

TOXIC EFFECTS :: Cardiac - other changes Blood - changes in spleen Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 273 gm/kg/13W-C

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 41700 ug/m3/4H/30D-I

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 20 mg/kg

SEX/DURATION :: female 4 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 750 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 169,129,1986 *** REVIEWS *** TOXICOLOGY REVIEW FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 15,611,1977 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M0609 No. of Facilities: 378 (estimated) No. of Industries: 14 No. of Occupations: 28 No. of Employees: 6740 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M0609 No. of Facilities: 10912 (estimated) No. of Industries: 89 No. of Occupations: 97 No. of Employees: 177946 (estimated) No. of Female Employees: 69887 (estimated)

香草醛安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H319

[ 警示性声明 ]:
P305 + P351 + P338

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xn:Harmful

[ 风险声明 (欧洲) ]:
R22

[ 安全声明 (欧洲) ]:
S24/25-S22

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
1

[ RTECS号 ]:
YW5775000

[ 海关编码 ]:
2912410000

香草醛合成路线

详细合成路线

香草醛上下游产品

香草醛上游产品

香草醛下游产品

香草醛制备

1.将N，N-二甲基苯胺用盐酸酸化成盐，用亚硝酸钠硝化掉得对亚硝基-N，N-二甲苯胺盐酸盐。将其与愈创木酚、甲醛在41-43℃缩合。然后用苯萃取。第一次蒸馏，用苯重结晶，再进行第二次蒸馏，用水重结晶。50℃干燥得成品。亚硫酸纸浆废液中，含有桦柏醇结构单位的木质素磺酸盐，在碱性条件下氧化，然后水解可得到香草醛。原料消耗（kg/t）愈创木酚（98%） 1460亚硝酸钠 640N，N-二甲基苯胺（98%） 974盐酸（30%） 6000甲醛（99%） 320

2.将N,N-二甲基苯胺在30%的盐酸、亚硝酸钠存在下进行亚硝化反应，所得亚硝基化合物与邻甲氧基苯酚、甲醛进行缩合反应，再水解制得香草醛粗品：

含有对氨基N,N- 二甲基苯胺盐酸盐的粗品香草醛经萃取，二次蒸馏，用石油醚重结晶，干燥得到提纯。
3.将2- 甲氧基苯酚、乙醛酸钠、氢氧化钠在搅拌下加到水中，维持25℃反应24h ［2-甲氧基苯酚∶乙醛酸钠∶氢氧化钠∶水＝40∶24∶13 ∶ 950（质量比）］。反应结束后，用硫酸调节混合物ph值为5，用苯萃取出未反应的2-甲氧基苯酚。然后于高压釜中与水、氢氧化钠、氧化铜混合，加175℃，控制压力303.9kPa ，边搅拌边以2L/min速度通入空气90min进行氧化反应。反应结束后，过滤除去氧化铜。所得反应产物用硫酸ph值为1.5，用甲基异丁基酮萃取5次，分去水层后，再用硫酸调ph值为7.0，于20℃下用甲基异丁基酮再萃取5次，分去水层。加热甲基异丁基酮层以蒸出甲基异丁基酮，之后，在666Pa下蒸馏，收集149～151℃馏分为目的产物香草醛成品。

4.以丁香油为基本原料，用酚钠盐法单离出丁香酚以后，按下列反应制取香兰素。
丁香酚异构化生成异丁香酚：

异丁香酚乙酰化生成乙酰基异丁香酚:

乙酰基异丁香酚氧化反应生成乙酰基香兰素：

乙酰基香兰素水解生成香兰素钾盐:

香兰素钾盐酸化生成香兰素：

② 以黄樟油素为原料制取。黄樟油素异构化生成异黄樟油素酚醚：

异黄樟油素酚醚甲基化、水解和氧化反应生成香兰素

③ 以木质素为原料制取。近年来许多国家采用造纸工业亚硫酸纸浆废液中的木质素来生产香兰素，由于原料来源丰富，是很有发展前途的合成方法。其反应过程如下：

④ 以愈创木酚为原料制取。

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香草醛海关

[ 海关编码 ]: 2912410000

[ 中文概述 ]:
HS: 2912410000. 香草醛(3-甲氧基-4-羟基苯甲醛). 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最低关税:5.5%. 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 四聚甲醛报明外观

[ Summary ]:
HS: 2912410000. 4-hydroxy-3-methoxybenzaldehyde. VAT:17.0%. tax rebate rate:13.0%. supervision conditions:None. MFN tarrif:5.5%. general tariff:30.0%

香草醛文献

Antimicrobial activity of natural products from the flora of Northern Ontario, Canada.

Pharm. Biol. 53(6) , 800-6, (2015)

The number of multidrug resistant (MDR) microorganisms is increasing and the antimicrobial resistance expressed by these pathogens is generating a rising global health crisis. In fact, there are only ...

Detoxification of biomass hydrolysates with nucleophilic amino acids enhances alcoholic fermentation.

Bioresour. Technol. 186 , 106-13, (2015)

Carbonyl compounds generated in biomass pretreatment hinder the biochemical conversion of biomass hydrolysates to biofuels. A novel approach of detoxifying hydrolysates with amino acids for ethanol pr...

Effect of selected Saccharomyces cerevisiae yeast strains and different aging techniques on the polysaccharide and polyphenolic composition and sensorial characteristics of Cabernet Sauvignon red wines.

J. Sci. Food Agric. 95 , 2132-44, (2015)

The objective of this work was to study the effect of two Saccharomyces cerevisiae yeast strains with different capabilities of polysaccharide liberation during alcoholic fermentation in addition to s...

更多文献

香草醛相关知识

香草醛应用和制备

2022-05-09 19:22:01

香草醛学名3-甲氧基-4-羟基苯甲醛白色至淡黄色结晶性粉末或针状结晶，有香草豆的特殊香气，微溶于苯，易溶于乙醇、乙醚、氯仿和冰醋酸。一克香草醛在14℃可溶于90—100毫升水中，在80℃可溶于20毫升水中。在潮湿空气中慢慢氧化成香草酸；与钠汞齐作用或催化还原生成香草醇；与氯化铁作用呈蓝紫色；与溴作...

香草醛