2-Methyl-1,4-naphthoquinone β-甲萘醌

CAS 58-27-5 MFCD00001681

化学结构图

58-27-5
SMILES: CC1=CC(=O)c2ccccc2C1=O

化学属性

Mol. FormulaC11H8O2
Mol. Weight172
Melting Point105-107
TSCAYes
Density1.225
Solubility不溶
Stability对光敏感
Appearance crystalline 白色结晶或结晶性粉末，几乎无臭，有吸湿性，遇光变色。易溶于水，微溶于乙醇，不溶于乙醚和苯。

别名和识别编码

Chemical Name2-Methyl-1,4-naphthoquinone
CAS Number58-27-5
Alfabeta NameMETHYLNAPHTHOQUINONE 2-
MDL NumberMFCD00001681
Synonym {uni_hamburg} 3-Methyl-1,4-naphthoquinone K-Vitan MNQ 甲萘醌 {Chemical Koaxin 甲萘醌亚硫酸氢钠,ME Kaergona 2-Met 2-METHYL-1,4-NAPHTHAQUINONE Menadione 2-Methyl-1,4-naphthochinon 维生素K3(水溶性) Kappaxan Menadione, Vitamin K3 Kipca, oil soluble Hemodal ######## MENAPHTHON Menaphthon 2-Methyl-1,4-Naphthalenedione Aquakay Kipca 2-methyl-(1,4)naphthoquinone C11H8O2 (2-methyl-1,4-naphthoquinone) {uni_hambur 2-甲基-1,4-萘醌 维生素 K3 2-methyl-1,4-dihydronaphthalene-1,4-dione 2-METHYL-1,4-DIHYDRONAPHTHALENE-1,4-DIONE 2-甲基-1,4-萘酚喹酮
PubChem Substance ID4055
EC Number200-372-6
Beilstein Registry Number1908453
Reaxys-RN1908453
Merck Number5831
Chemical Name Translationβ-甲萘醌
Wiswesser Line NotationL66 BV EVJ C1
LabNetwork Molecule IDLN00158603
InChIInChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
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分类

  • {SNA} Analytical Standards, EP Standards, EP Standards L - M, Pharmacopeia & Metrological Institutes Standards, 分析/色谱
  • {SNA} Biochemicals and Reagents, Cell Stress, Nitric Oxide and Cell Stress, Oxidative Stress Proteins and Reagents, Prenols, Vitamin K, Vitamin K3, Vitamins,

产品应用

  • 生化研究。该品与亚硫酸氢钠加成即得维生素K3。

相关文献及参考

  • Cossarizza, A., et al., Simultaneous analysis of reactive oxygen species and reduced glutathione content in living cells by polychromatic flow cytometry. Nat. Protoc. 4 , 1790-7, (2009) 摘要
  • Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010),
  • Hu, W., et al.: Anal. Biochem., 398, 245 (2010),
  • Merck 14 ,5831
  • Merck:14,5831
  • Merck:14,5831 Beilstein:7(2)656
  • Sakamoto, S., et al.: Anal. Bioanal. Chem., 396, 2955 (2010),
  • Short: II/27B
  • [1]. http://en.wikipedia.org/wiki/Menadione

安全信息

Warnings IRRITANT
GHS Symbol
WGK Germany3
Hazard Codes Xn
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H302 Harmful if swallowed 吞食有害
  • H319 Causes serious eye irritation 严重刺激眼睛
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
RTECSQL9100000
Precautionary statements
  • 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。
  • 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
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P301+P312+P330
  • 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。
Signal word
Safety Statements
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
  • 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；
  • S24 Avoid contact with skin 避免皮肤接触；
  • 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
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Storage condition Store at RT. Light Sensitive 密封阴凉干燥避光保存。 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1860 mg/kg/27W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Skin and Appendages - tumors
   Tumorigenic - tumors at site of application
REFERENCE :
   BJCAAI British Journal of Cancer.  (Macmillan Press Ltd., Houndmills,
   Basingstoke, Hants. RG21 2XS, UK)  V.1-    1947-  Volume(issue)/page/year:
   7,482,1953

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 8400 mg/kg/21W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Skin and Appendages - tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   19,413,1959

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 75 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   18,185,1971

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 230 mg/kg
TOXIC EFFECTS :
   Vascular - other changes
REFERENCE :
   JPETAB Journal of Pharmacology and Experimental Therapeutics.  (Williams &
   Wilkins Co., 428 E. Preston St., Baltimore, MD 21202)  V.1-    1909/10-
   Volume(issue)/page/year: 75,111,1942

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 50 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: AD691-490

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Bird - chicken
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   PSEBAA Proceedings of the Society for Experimental Biology and Medicine.
   (Academic Press, Inc., 1 E. First St., Duluth, MN 55802)  V.1-    1903/04-
   Volume(issue)/page/year: 43,125,1940

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

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 6 ppm
REFERENCE :
   POASAD Proceedings of the Oklahoma Academy of Science.  (Oklahoma Academy of
   Science, c/o Executive Secretary-Treasurer, Southwestern Oklahoma State
   Univ., Weatherford, OK 73096) V.1-    1910/1920-  Volume(issue)/page/year:
   34,114,1953

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Human Fibroblast
DOSE/DURATION           : 20 umol/L
REFERENCE :
   TOLED5 Toxicology Letters.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1977-  Volume(issue)/page/year: 28,37,1985

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - mouse Embryo
DOSE/DURATION           : 750 ug/L
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 16,477,1995

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - hamster Cells - not otherwise specified
DOSE/DURATION           : 15 umol/L
REFERENCE :
   BCPCA6 Biochemical Pharmacology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1958-  Volume(issue)/page/year:
   42,1961,1991

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 30 nmol/plate
REFERENCE :
   BBRCA9 Biochemical and Biophysical Research Communications.  (Academic
   Press, Inc., 1 E. First St., Duluth, MN 55802)  V.1-    1959-
   Volume(issue)/page/year: 94,737,1980

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 10 nmol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Build

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 20 mg/kg
SEX/DURATION            : female 8 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   TOIZAG Toho Igakkai Zasshi.  Journal of Medical Society of Toho University.
   (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143,
   Japan)  V.1-    1954-  Volume(issue)/page/year: 8,175,1961

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 3 gm/kg
SEX/DURATION            : female 1-20 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   NYKZAU Nippon Yakurigaku Zasshi.  Japanese Journal of Pharmacology. (Nippon
   Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho,
   Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40-    1944- Volume(issue)/page/year:
   69,285,1973

其他信息

  • 用途二:生化研究，临床药物属脂溶性维生素，临床作为止血药。
  • 所属类别二:食品添加剂: 营养强化剂（营养增补剂）: 维生素
  • 所属类别三:饲料添加剂: 维生素添加剂
  • 上游原料:三氧化铬 --> 重铬酸钠 --> 重铬酸钾 --> 1,3-丁二烯 --> 1-甲基萘 --> 2-甲基萘 --> 甲基萘
  • 用途一:饲料添加剂原料，主要能促进畜禽肝脏合成凝血酶原，并促进血浆凝血因子在肝脏内合成
  • 参考质量标准二:GB7294—87 含量(以C11H9O5SNa·3H2O计)/% 60.0～75.0 亚硫酸氢钠含量
  • 方法二:2-甲基萘经铬酐氧化，再与亚硫酸氢钠反应制得。
  • MOL 文件:58-27-5.mol
  • 溶于乙醇(1 G/60 ML) 、苯(1 G/10 ML)、氯仿、四氯化碳和植物油(1 G/50 ML)等，不溶于水。遇光或铁质分解变质，能随水蒸气挥发。
  • 敏感性:Light Sensitive
  • 用途四:该品与亚硫酸氢钠加成即得维生素K3。
  • 用途五:生化研究。该品与亚硫酸氢钠加成即得维生素K3。
  • 参考质量标准一:含量≥94%，磺酸甲萘醌合格。
  • 用途三:维生素K3主要用作禽类饲料强化剂。用量1-5mg/kg。
  • color:yellow
  • 使用限量:GB 14880—94：婴幼儿食品，420～750,v．g/kg。
  • 甲萘醌价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 SM562501 维生素K3 25g 515元 2011/04/16 M0373 2-甲基-1,4-萘醌 2-Methyl-1,4-naphthoquinone 250G 2310元 2011/04/16 M0373 2-甲基-1,4-萘醌 2-Methyl-1,4-naphthoquinone 25G 469元
  • Alfa Aesar:2-甲基-1,4-萘醌,98% 2-Methyl-1,4-naphthoquinone, 98%(58-27-5)
  • 所属类别一:生物化学品: 生化试剂: 辅酶和维生素
  • 图谱信息:甲萘醌(58-27-5)红外图谱(IR2) 甲萘醌(58-27-5)核磁图( 13 CNMR) 甲萘醌(58-27-5)质谱(MS) 甲萘醌(58-27-5)核磁图( 1 HNMR) 甲萘醌(58-27-5)红外图谱(IR1)
  • 方法一:以邻甲基萘醌为原料，经冰醋酸和铬酐氧化后在乙醇中与亚硫酸氢钠加成而得。
  • F:8
  • 方法三:有两种生产工艺。1.甲基萘用铬酐氧化而得。将2-甲基萘溶解于冰醋酸中，搅拌冷却到40℃以下，缓缓加入铬酐与等量水的混和液，使温度维持在35-40℃。加毕，在40℃保温0.5h，升温到70℃保温45min，再升温到85℃保温15min，将反应物倾入大量水中，不断搅拌下沉淀出2-甲萘醌。过滤，滤饼反复用水洗，至水溶液无酸味，滤干得2-甲萘醌。收率51%。2-甲基萘也可用重铬酸钠、重铬酸钾氧化收率大致相同。2.由甲苯醌与丁二烯环合得到2-甲基萘氢醌，再经铬酸氧化而得。将甲苯醌加入冰醋酸中溶解，通入丁二烯，在20℃以下通至所需量。密闭静置20h后，加热使剩余的丁二烯逸出，继续加热至110℃左右回流3h，再减压蒸馏回收冰醋酸约30%。然后冷却至40℃以下，缓缓加入铬酸与等量水的混合液，使温度保持在65-70℃，加毕，在70-80保温1h而生成甲萘醌。
  • Acros Organics:2-甲基-1,4-萘醌酮/甲萘醌/维生素K3 2-Methyl-1,4-naphthoquinone, 98%(58-27-5)
  • TCI Shanghai:2-甲基-1,4-萘醌 2-Methyl-1,4-naphthoquinone,>;98.0%(LC)(T)(58-27-5)
  • Sigma Aldrich:58-27-5(sigmaaldrich)

系列性分类

  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Prenols - Lipids
  5. Vitamin K - Prenols
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Alphabetic - Analytical Standards
  4. M - Alphabetic
  5. MEA - MES - M
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Food & Beverage Standards - Chromatography
  5. Vitamins - Food & Beverage Standards
  6. Fat-Soluble Vitamins - Vitamins
  7. Vitamin K - Fat-Soluble Vitamins
  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Vitamins - Nutrition Research
  4. Vitamin K - Vitamins
  5. Vitamin K3 - Vitamin K
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Amino Acids 氨基酸
  4. Modified Amino Acids - Amino Acids
  5. Other Ester of Amino Acids
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Substrates
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Vitamins
  4. Vitamin E
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Peptides and Proteins
  5. Other Peptides
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Lipids
  4. Prenols
  5. Vitamin E
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Nitric Oxide and Cell Stress
  5. Cell Stress
  6. Mitochondrial Inhibitors
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Peptides and Proteins
  5. Proteins for Cell Biology
  6. Kinases and Phosphatases
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Proteins and Derivatives
  4. Proteins for Cell Biology
  5. Kinases and Phosphatases
  6. Protein Kinase Inhibitors and Related Products
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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