4,4’-(2,3-Dimethylbutane-1,4-Diyl)Bis(Benzene-1,2-Diol) 4,4’-(2,3-二甲基丁-1,4-二基)双(苯-1,2-二醇)

CAS 500-38-9 MFCD00002206

化学结构图

500-38-9
SMILES: C[C@@H](Cc1ccc(O)c(O)c1)[C@H](C)Cc1ccc(O)c(O)c1

化学属性

Mol. FormulaC18H22O4
Mol. Weight302
Melting Point184-186
TSCANo
Appearance Solid powder 抗氧化效果较好，对防霉亦有效。与柠檬酸、抗坏血酸合用有增效作用。 白色至灰白色结晶性粉末。熔程183～185℃。难溶于水。稍溶于热水。易溶于乙醇、乙醚、甘油、丙二醇。油脂中约溶解0.5%。
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical Name4,4’-(2,3-Dimethylbutane-1,4-Diyl)Bis(Benzene-1,2-Diol)
MDL NumberMFCD00002206
CAS Number500-38-9
Synonym 1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane, 4,4′-(2,3-Dimethyltetramethylene)dipyrocatechol, Masoprocol, NDGA
PubChem Substance ID87567422
EC Number207-903-0
Beilstein Registry Number2056826
Merck Number6693
Chemical Name Translation4,4’-(2,3-二甲基丁-1,4-二基)双(苯-1,2-二醇)
Reaxys-RN9803564
InChIKeyHCZKYJDFEPMADG-TXEJJXNPSA-N
Wiswesser Line NotationQR BQ D1Y1&Y1&1R CQ DQ
LabNetwork Molecule IDLN00242107
InChIInChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3/t11-,12+
FormulaC18H22O4
IUPAC Name4,4'-((2R,3S)-2,3-dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
Canonical SMILESC[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC2=CC=C(O)C(O)=C2
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分类

  • {SNA} Bioactive Small Molecules, Building Blocks, Cell Biology, Chemical Synthesis,
  • {SNA} Building Blocks,
  • {SNA} A to C, Application Index, Arachidonic Acid Cascade, Bioactive Small Molecule Alphabetical Index, Biochemicals and Reagents, Cell Signaling Enzymes, Cyclooxygenase, Cyclooxygenase (COX) Enzymes, Cyclooxygenase Inhibitors, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, L to O, Lipids in Cell Signaling, Lipoxygenase, N, Phenols, Phytochemicals by Chemical Classification, 生物活性小分子, 细胞信号转导和神经科学, 细胞生物学, 营养研究,
  • {SNA} Bu

产品应用

  • INSM-18, also known as nordihydroguaiaretic acid, NDGA and masoprocol, is a naturally occurring antioxidant dicatechol originally derived from the creosote bush Larrea divaricatta with antipromoter, anti-inflammatory, and antineoplastic activities. NDGA directly inhibits activation of two receptor tyrosine kinases (RTKs), the insulin-like growth factor receptor (IGF-1R) and the c-erbB2/HER2/neu receptor, resulting in decreased proliferation of susceptible tumor cell populations.

相关文献及参考

  • [2]. Lu F, et al. Virtual Screening for Potential Allosteric Inhibitors of Cyclin-Dependent Kinase 2 from Traditional Chinese Medicine. Molecules. 2016 Sep 21;21(9). pii: E1259.
  • [3]. Zhang H, et al. Nordihydroguaiaretic acid improves metabolic dysregulation and aberrant hepatic lipid metabolism in mice by both PPARα-dependent and -independent pathways. Am J Physiol Gastrointest Liver Physiol. 2013 Jan 1;304(1):G72-86.
  • Naturally-occurring antioxidant.
  • [1]. West M, et al. The arachidonic acid 5-lipoxygenase inhibitor Nordihydroguaiaretic acid inhibits tumor necrosis factor alpha activation of microglia and extends survival of G93A-SOD1 transgenic mice. J Neurochem. 2004 Oct;91(1):133-43.
  • [1]. West M, et al. The arachidonic acid 5-lipoxygenase inhibitor Nordihydroguaiaretic acid inhibits tumor necrosis factor alpha activation of microglia and extends survival of G93A-SOD1 transgenic mice. J Neurochem. 2004 Oct;91(1):133-43.
  • [2]. Lu F, et a

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
RTECSUX1750000
Precautionary statements
  • 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
Signal word Warning
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
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
  • R22 Harmful if swallowed 吞咽有害
Hazard Codes Xn
Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). Freezer (-20°C) 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - guinea pig
DOSE/DURATION           : 830 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AFREAW Advances in Food Research.  (Academic Press, Inc., 1 E. First St.,
   Duluth, MN 55802) V.1-32, 1948-88.  Volume(issue)/page/year: 3,197,1951

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 550 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AFREAW Advances in Food Research.  (Academic Press, Inc., 1 E. First St.,
   Duluth, MN 55802) V.1-32, 1948-88.  Volume(issue)/page/year: 3,197,1951

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JAOCA7 Journal of the American Oil Chemists' Society.  (Champaign, IL)
   V.24-56, 1947-79.  Volume(issue)/page/year: 54,239,1977

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JAOCA7 Journal of the American Oil Chemists' Society.  (Champaign, IL)
   V.24-56, 1947-79.  Volume(issue)/page/year: 54,239,1977

TYPE OF TEST            : Sister chromatid exchange
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 35300 ug/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 412,139,1998

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 13500 nmol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 412,139,1998

TYPE OF TEST            : Mutation test systems - not otherwise specified
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 70700 ug/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 412,139,1998

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 3600 nmol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 412,139,1998

其他信息

  • 图谱信息:去甲二氢愈创木酸(500-38-9)红外图谱(IR1) 去甲二氢愈创木酸(500-38-9)质谱(MS) 去甲二氢愈创木酸(500-38-9)红外图谱(IR2) 去甲二氢愈创木酸(500-38-9)核磁图( 13 CNMR)
  • 去甲二氢愈创木酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30228980 双(3，4-二羟基)-2，3-二甲基丁烷 5g 2412元 2011/04/16 D0800 4,4'-(2,3-二甲基四亚甲基)二邻苯二酚 Nordihydroguaiaretic Acid 5G 3500元 2011/04/16 D0800 4,4'-(2,3-二甲基四亚甲基)二邻苯二酚 Nordihydroguaiaretic Acid 1G 1010元
  • Sigma Aldrich:500-38-9(sigmaaldrich)
  • TCI Shanghai:4,4'-(2,3-二甲基四亚甲基)二邻苯二酚 4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol,>;95.0%(LC)(500-38-9)
  • 用途一:抗氧化剂。 按日本规定，限用于油脂及奶油，最大用量为0.1g/kg。使用时将油脂加热至约115℃。现很少采用。
  • 毒性:ADI未规定(FAO/WHO，2001)。 LD 50 2000mg/kg(大鼠，经口)。 美国禁用(FDA，§189．165，2000)。
  • 上游原料:愈创木脂
  • MOL 文件:500-38-9.mol
  • 含量分析:取试样1.00g，用甲醇稀释至溶液的最终浓度为lmg/100ml，盛于lcm石英比色皿中，读取在波长284nm处的吸光度A。 正二氢愈创酸含量(%)一磺蕃主揣×100
  • 方法一:由愈创树脂的成分愈创木脂酸二甲醚加氢脱甲基而得。也可由山毛榉叶子用碱溶提取，在酸性条件下结晶，再加水分解而得。
  • Acros Organics:去甲二氢愈创木酸 Nordihydroguaiaretic acid, 95%(500-38-9)
  • 鉴别试验:溶解性 易溶于乙醇和乙醚，溶于116℃丙二醇。按OT-42方法测定。 熔点约184℃，按常规方法测定。 取氯化铁乙醇试液(TS-102)2ml和2，2一二吡啶试液(TS-41)2ml，加入含0.5%试样的50%乙醇液5ml中，应呈深樱红色。 取1%试样的75%乙醇液5ml，加浓氨试液(TS-13)1ml，应呈黄色。 取0.5%试样的50%乙醇液10ml，加1%氢氧化钡[Ba(OH)2?H2O3的沸水液1.5ml。应呈深蓝色，并可保持约1h。 取10%氢氧化钠10ml，加入0.5%试样的
  • 参考质量标准:FAO/WHO，1992 含量 95%～102% 砷(以As计，GT-3) ≤3mg/kg 铅(GT-18) ≤10mg/kg 重金属(以Pb计，GT-16) ≤30mg/kg
  • Alfa Aesar:去甲二氢愈创木酸,97% Nordihydroguaiaretic acid, 97%(500-38-9)

系列性分类

  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Phytochemicals by Chemical Classification - Nutrition Research
  4. Plant Extracts - Phytochemicals by Chemical Classification
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. N - Bioactive Small Molecules
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Oxygen Compounds 氧化合物
  5. Polyols - Oxygen Compounds
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Enzyme Inhibitors - Enzymes, Inhibitors, and Substrates
  5. Enzyme Inhibitors by Type - Enzyme Inhibitors
  6. Substrate Analogs - Enzyme Inhibitors by Type
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Application Index - Enzymes, Inhibitors, and Substrates
  5. Cell Signaling Enzymes - Application Index
  6. Cyclooxygenase (COX) Enzymes - Cell Signaling Enzymes
  7. Cyclooxygenase Inhibitors - Cyclooxygenase (COX) Enzymes
  1. Medical Research Areas
  2. Protein Tyrosine Kinase
  3. HER2
  1. Medical Research Areas
  2. Metabolism
  3. Lipoxygenase  (脂氧合酶)

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