3-Methoxy-4-hydroxybenzaldehyde 3-甲氧基-4-羟基苯甲醛

CAS 121-33-5 MFCD00006942

化学结构图

121-33-5
SMILES: COc1cc(C=O)ccc1O

化学属性

Mol. FormulaC8H8O3
Mol. Weight152.15
Boiling Point170°C at 760 mmHg
Melting Point81-83°C
Density1.06
Flash Point153°C(lit.)
TSCAYes
Vapor Density5.3 (vs air)
Vapor Pressure>;0.01 mmHg ( 25 °C)
Solubility10 G/L (25 ºC)
Stability对光、空气、湿度敏感

别名和识别编码

Chemical Name3-Methoxy-4-hydroxybenzaldehyde
CAS Number121-33-5
Alfabeta NameHYDROXYMETHOXYBENZALDEHYDE 43---
MDL NumberMFCD00006942
Synonym Vanillin {LY} Vanillin {} {LY} Vanillin {} {} {LY} Vanillin {} {} {} {LY} Vanillin {} {} {} {} {LY} Vanillin {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Vanillin {} {} {} {} {} {} {} {} {} {} {} {} {
EC Number204-465-2
Beilstein Registry Number472792
PubChem Substance ID1183
Reaxys-RN472792
Merck Number9932
Chemical Name Translation3-甲氧基-4-羟基苯甲醛
Wiswesser Line NotationVHR DQ CO1
LabNetwork Molecule IDLN00335569
InChIInChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
Canonical SMILESO=CC1=CC=C(O)C(OC)=C1
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分类

  • {SNA} Aldehydes,
  • {SNA} Alcoholic & Nonalcoholic Beverages, Aldehyde, All Alphabetically Sorted, Alphabetical Index of Analytical Standards, Analytical Standards, Analytical/Chromatography, Animal Products, Chromatography, Clove, Coffee, Flavors and Fragrances, Food & Beverage Standards, Food Products & Beverages, Fragrance Allergens in Cosmetic Products,
  • {SNA} Alphabetical Listings,
  • {SNA} Alphabetical Listings, Certified Food Grade Products, F&F Ingredients in Drum Quantities (25-200 kg), Flavors and Fragrances, Halal Certified Products, Kosher Certified Products, O - Z, O-Z, Q-Z, R-Z
  • {SNA} Alph

产品应用

  • An intermediate and analytical reagent.

相关文献及参考

  • [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.
  • Merck: 14,9932
  • Merck: 14,9932 Beilstein: 8,IV,1763
  • Nazeruddin, G., et al.: Res. J. Pharm., Biol. Chem. Sci., 2, 71 (2011),
  • Short: III/35D2
  • Yang, X., et al.: Biores. Technol., 102, 3498 (2011),
  • [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.
  • [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

安全信息

Warnings IRRITANT
GHS Symbol
WGK Germany1
Hazard statements
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H302 Harmful if swallowed 吞食有害
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
  • H341 Suspected of causing genetic defects 怀疑导致遗传性缺陷
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
RTECSYW5775000
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P312+P330
  • P301+P330+P331+P310
  • P302+P350
  • P302+P352+P332+P313+P362+P364
  • P304+P340
  • P304+P340+P310
  • P305+P351+P338
  • P305+P351+P338+P310
  • P305+P351+P338+P337+P313
  • P308+P313
  • P332+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P403+P233
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Warning
Hazard Codes Xn Xi
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
Risk Statements
  • R20/22 Harmful by inhalation and if swallowed 吸入和不慎吞咽有害
  • R22 Harmful if swallowed 吞咽有害
  • R36 Irritating to eyes 刺激眼睛
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
  • R62 Possible risk of impaired fertility 有削弱生殖能力的危险
  • R68 Possible risk of irreversible effects 可能有不可挽回的作用的危险
Storage condition 2-8°C, stored under nitrogen {LY} 2-8°C, stored under nitrogen Air & Light Sensitive {} {LY} 2-8°C, stored under nitrogen {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY
UN Number 2924
Packing GroupII
Hazard Class3/8
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
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: OTS0533712

{hazard_com

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

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
REFERENCE :
   FCTXAV Food and Cosmetics Toxicology.  (London, UK)  V.1-19, 1963-81.  For
   publisher information, see FCTOD7.  Volume(issue)/page/year: 2,327,1964

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
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: OTS0536271

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)
REFERENCE :
   FCTXAV Food and Cosmetics Toxicology.  (London, UK)  V.1-19, 1963-81.  For
   publisher information, see FCTOD7.  Volume(issue)/page/year: 2,327,19

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 4 mmol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 190,221,1987

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

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
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
REFERENCE :
   JSICAZ Journal of Scientific and Industrial Research, Section C: Biological
   Sciences.  (New Delhi, India)  V.14-21, 1955-62.  For publisher information,
   see IJEBA6.  Volume(issue)/page/year: 19,264,1960

其他信息

  • 所属类别二:食品添加剂: 食用香料(增香剂): 天然等同香料和人造香
  • 作用与用途:香兰素是重要的食用香料之一,是食用调香剂,具有香荚兰豆香气及浓欲的奶香,是食品添加剂行业中不可缺少的重要原料,广泛运用在各种需要增加奶香气息的调香食品中, 如蛋糕、冷饮、巧克力、糖果、饼干、方便面、面包以及烟草、调香酒类、牙膏、 肥皂、香水化妆品、冰淇淋、饮料以及日用化妆品中起增香和定香作用。还可用于香皂、牙膏、香水、橡胶、塑料、医药品。符合F
  • 概述:香兰素是人类所合成的第一种香精,由德国的M·哈尔曼博士与G·泰曼博士于1874年合成成功的。通常分为甲基香兰素和乙基香兰素。甲基香兰素(vanillin),化学名3-甲氧基-4-羟基苯甲醛,外观白色或微黄色结晶,具有香荚兰香气及浓郁的奶香,为香料工业中最大的品种,是人们普遍喜爱的奶油香草香精的主要成份。其用途十分广泛,如在食品、日化、烟草工业中作为香原料、矫味剂或定香剂,其中饮料、糖果、糕点、饼干、面包和炒货等食品用量居多。目前还没有相关报道说香兰素对人体有害。 乙基香兰素为白色至微黄色针状结晶或结晶性粉末,类似香荚兰豆香气,香气较甲基香兰素更浓。属广谱型香料,是当今世界上最重要的合成香料之一,是食品添加剂行业中不可缺少的重要原料,其香气是香兰素的3-4倍,具有浓郁的香荚兰豆香气,且留香持久。广泛用于食品、巧克力、冰淇淋、饮料以及日用化妆品中起增香和定香作用。另外乙基香兰素还可做饲料的添加剂、电镀行业的增亮剂,制药行业的中间体。
  • 下游产品:异戊醇 --> 丁酸 --> 2-甲氧基-4-(2-氨基乙基)苯酚 --> 4,5-二甲氧基-3-碘苯甲醛 --> 黄檀素 --> 姜黄素 --> 藜芦醛 --> 邻香草醛 --> 3,4,5-三甲氧基苯甲醛 --> 4-苄氧基-3-甲氧基苯甲醛 --> 天然辣椒素 --> 3-羟基-4-甲氧基苯甲醛 --> 卡别多巴 --> 甲基多巴 --> 1,2,4-三甲氧基苯 --> 敌菌净 --> 2-(3,4-二羟基苯基)乙胺 --> 2-甲氧基-4-(2-硝基乙烯)酚 --> 2,3-二甲氧基苯甲醛 --> 柠檬草油 --> 扁叶香果兰(VANILLA PLANIFOLIA)果 --> 2,3-二溴-4-羟基-5-甲氧基苯甲醛 --> 反式阿魏酸 --> 香兰素胺盐酸盐 --> 5-溴香兰素 --> 3,4-二羟基苯甲酸 --> 4-(2-氨基乙基)-2-甲氧基苯酚 --> 丙酸香茅酯 --> 5-羟基香草
  • 用途四:GB 2760 1996规定为允许使用的食用香料。广泛用于配制香草、巧克力、奶油等型香精,用量可达25%~30%,或直接用于饼干、糕点,用量0.1%~0.4%,冷饮0.01%~0.3%,糖果0.2%~0.8%,尤其是含乳制品。
  • 行业发展状况:我国是世界香兰素出口大国,2002年国内需求量2350吨,占产量的30%,其余70%用于出口。而1988年仅出口273吨,1993年为1700吨,2002年为4653吨。1993~2002年,我国香兰素出口量年均增长率为12%,在北美、欧洲、东南亚等地市场享有良好信誉。 2012年全球香兰素需求总量在17500吨左右,其中发达国家的需求处于平衡状态,而发展中国家对香兰素的需求量在明显增加,使得香兰素的总需求量仍处于增长期。其中我国的实际需求总量目前已达到3000吨左右,目前人均使用量仍稍低于全球人均使用量。 国内主要供应商嘉兴市中华化工有限责任公司是当今全球最大的香兰素专业制造商,2014年公司年产甲基香兰素10000吨、乙基香兰素2000吨,其中80%以上产品用于出口。 国外主要有法国罗地亚公司、挪威鲍利甚公司、日本宇部兴产3家香兰素生产商。其中,法国罗地亚是全球最知名的香兰素生产企业,年产能力为8000吨,装置分布在法国、美国。 目前除挪威鲍利格公司采用木质素法生产香兰素外,国内与国际公司均采用愈创木酚-乙醛酸法生产香兰素。
  • 用途三:香兰素是我国规定允许使用的食用香料,可作定香剂,是配制香草型香精的主要原料。也可直接用于饼干、糕点、糖果、饮料等食品的加香。用量按正常生产需要,一般在巧克力中970mg/kg;口香糖中270mg/kg;糕点、饼干中220mg/kg;糖果中200mg/kg;调味品中150mg/kg~冷饮中95mg/kg。
  • 含量分析:方法一 用紫外吸收分光光度法分析(参见GT-29)。 标准溶液的制备 准确称取药用参比标准香兰素

系列性分类