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58-27-5 分子结构
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2-methyl-1,4-dihydronaphthalene-1,4-dione

ChemBase编号:55
分子式:C11H8O2
平均质量:172.18002
单一同位素质量:172.0524295
SMILES和InChIs

SMILES:
O=C1c2c(C(=O)C=C1C)cccc2
Canonical SMILES:
O=C1C=C(C)C(=O)c2c1cccc2
InChI:
InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChIKey:
MJVAVZPDRWSRRC-UHFFFAOYSA-N

引用这个纪录

CBID:55 http://www.chembase.cn/molecule-55.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
2-methyl-1,4-dihydronaphthalene-1,4-dione
IUPAC传统名
menadione
商标名
Synkavite
Synkayvite
Kappaxin
Klottone
Panosine
Kolklot
Kayklot
别名
2-甲基-1,4-萘醌
维生素 K3
甲萘醌
甲萘醌
甲萘醌 (K3)
2-甲基-1,4-萘醌
Menadione
2-methylnaphthalene-1,4-dione
Vitamin K3
Vitamin K3
2-Methylnaphthoquinone
1,4-Dihydro-1,4-dioxo-2-methylnaphthalene
Aquakay
Aquinone
Hemodal
K-Thrombyl
K-Vitan
Kaergona
Kanone
Kappaxan
Kappaxin
Karcon
Kareon
Kativ-G
Kayklot
Kaykot
Kaynone
Kipca
Kipca-Oil Soluble
Klottone
Koaxin
Kolklot
MNQ
Menadion
Menaphthon
Menaquinone 0
Mitenon
Mitenone
NSC 4170
Panosine
Prokayvit
Synkay
Vitamin K3
Menadione (K3)
β-Methyl-1,4-naphthoquinone
2-Methyl-1,4-naphthodione
2-Methyl-1,4-Naphthalenedione
2-Methyl-1,4-naphthoquinone
Vitamin K 3
Menaphthone
Thyloquinone
Kayquinone
Vitamin K3
Menadione
Menadione
1,4-Dihydro-2-methylnaphthalene-1,4-dione
2-methyl-1,4-naphthoquinone
2-Methyl-1,4-naphthoquinone
CAS号
58-27-5
EC号
200-372-6
MDL号
MFCD00001681
Beilstein号
1908453
默克索引号
145831
PubChem SID
46505447
160963518
24871411
24897335
24897023
PubChem CID
4055
CHEBI ID
28869
ATC码
B02BA02
CHEMBL
590
Chemspider ID
3915
DrugBank ID
DB00170
KEGG ID
D02335
美国药典/FDA物质标识码
723JX6CXY5
维基百科标题
Menadione

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 12.936644  质子受体
质子供体 LogD (pH = 5.5) 1.8898684 
LogD (pH = 7.4) 1.8898674  Log P 1.8898685 
摩尔折射率 50.5403 cm3 极化性 18.667366 Å3
极化表面积 34.14 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.91  LOG S -2.53 
溶解度 5.04e-01 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Dichloromethane expand 查看数据来源
Dimethylformamide expand 查看数据来源
Ethyl Acetate expand 查看数据来源
Insoluble expand 查看数据来源
Insoluble in water expand 查看数据来源
Methanol expand 查看数据来源
oil: soluble expand 查看数据来源
外观
Bright yellow crystals expand 查看数据来源
Pale Yellow Solid expand 查看数据来源
yellow crystalline expand 查看数据来源
熔点
102-106 °C expand 查看数据来源
104-107°C expand 查看数据来源
105-107 expand 查看数据来源
105-107 °C(lit.) expand 查看数据来源
105-107°C expand 查看数据来源
105–107 °C expand 查看数据来源
97-99°C expand 查看数据来源
沸点
304.5 °C @ 760mmHg expand 查看数据来源
闪点
113.8 °C expand 查看数据来源
密度
1.225g/cm3 expand 查看数据来源
疏水性(logP)
1.6 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand 查看数据来源
Room Temperature (15-30°C), Protect from light expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
Irritant/Light Sensitive expand 查看数据来源
Light Sensitive expand 查看数据来源
RTECS编号
QL9100000 expand 查看数据来源
欧盟危险性物质标志
X expand 查看数据来源
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
22-36/37/38 expand 查看数据来源
安全公开号
26-36 expand 查看数据来源
26-36/37 expand 查看数据来源
TSCA收录
false expand 查看数据来源
expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
半数致死量
0.5 g/kg (oral, mouse) expand 查看数据来源
GHS危险声明
H301-H315-H319-H335 expand 查看数据来源
H302-H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A expand 查看数据来源
P261-P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand 查看数据来源
相关基因信息
human ... NQO1(1728) expand 查看数据来源
纯度
≥97.0% (HPLC) expand 查看数据来源
97% expand 查看数据来源
98% expand 查看数据来源
级别
analytical standard expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
包装
ampule of 1000 mg expand 查看数据来源
适用性
meets USP testing specifications expand 查看数据来源
特征
standard type fat soluble vitamin expand 查看数据来源
Empirical Formula (Hill Notation)
C11H8O2 expand 查看数据来源
分类
Genuine Natural Compounds expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02102259 external link
Yellow crystals
DrugBank -  DB00170 external link
Item Information
Drug Groups approved; nutraceutical
Description A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. [PubChem]
Indication The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.
Pharmacology Menadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K. The former, which is also known as phylloquinone, is synthesized by plants and can be found in such foods as spinach, broccoli, lettuce, and soybeans. The latter, sometimes alternatively referred to as menaquinone, is primarily produced by bacteria in the anterior part of the gut and the intestines. Vitamin K3, on the other hand, is one of the many manmade versions of vitamin K. Also called menadione, this yellowish, synthetic crystalline substance is converted into the active form of the K2 vitamin inside of the animal body. While a vitamin K deficiency can be dangerous, especially to infants that may easily suffer from extensive hemorrhaging, an overdose can be as equally detrimental. Newborns that are administered too great a dosage of vitamin K3 can suffer from kernicterus, a form of severe brain damage that may produce decreased movement, loss of appetite, seizures, deafness, mental retardation, and even death. This condition is associated with an abnormally high concentration of bilirubin, a bile pigment, in the tissues of the brain, which can be caused by the presence of K3. For this reason, K3 is less often utilized medically than it was in former times.
Toxicity Menadione (vitamin K3), which is not used as a nutritional supplemental form of vitamin K for humans, has been reported to cause adverse reactions, including hemolytic anemia. Large doses have also been reported to cause brain damage.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Variable and ranges from 10% to 80%
External Links
Wikipedia
PDRhealth
Selleck Chemicals -  S1949 external link
Research Area: Endocrinology
Biological Activity:
Menadione(Vitamin K3), a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone,after alkylation in vivo. Menadione (vitamin K3) is involved as a cofactor in the posttranslational gamma-carboxylation of glutamic acid residues of certain proteins in the body. These proteins include the vitamin K-dependent coagulation factors II (prothrombin), VII (proconvertin), IX (Christmas factor), X (Stuart factor), protein C, protein S, protein Zv and a growth-arrest-specific factor (Gas6). [1]
Sigma Aldrich -  M5625 external link
包装
25, 100 g in glass bottle
Biochem/physiol Actions
Menadione (Vitamin K3) is a synthetic analogue of of 1,4-naphthoquinone with a methyl group in the 2-position. Menadione is used as a phosphatase inhibitor and an inhibitor of mitochondrial DNA polymerase γ (pol γ). Menadione can be used as an oxidative injury (free radical generator) inducing agent.
Sigma Aldrich -  M57405 external link
包装
5, 100 g in glass bottle
Sigma Aldrich -  67900 external link
Other Notes
Review: Vitamin K and γ-carboxyglutamate biosynthesis1
Toronto Research Chemicals -  V676130 external link
Precursor to verious types of Vitamin K. Used as a micronutrient for livestock and pet foods.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • http://www.drugbank.ca/drugs/DB00170
  • Sakamoto, S., et al.: Anal. Bioanal. Chem., 396, 2955 (2010)
  • Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)
  • Hu, W., et al.: Anal. Biochem., 398, 245 (2010)
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专利

专利

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