异嗪皮啶 | 486-21-5

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 异嗪皮啶
• 中文别名: 7-羟基-6,8-二甲氧基苯并吡喃-2-酮；异秦皮定；异榛皮定
• 英文名称: isofraxidin
• 英文别名: 7-hydroxy-6,8-dimethoxy-2H-chromen-2-one；7-hydroxy-6,8-dimethoxychromen-2-one；6,8-dimethoxy-7-hydroxycoumarin；7-hydroxy-6,8-dimethoxycoumarin；isoferaxidin
• CAS: 486-21-5
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: HOEVRHHMDJKUMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  145～147℃
• 沸点：
  452.1±45.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：250 mg/mL（1125.16 mM）
• 保留指数：
  2085
• 稳定性/保质期：
  按规格使用和贮存，不会发生分解，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• WGK Germany：
  1
• RTECS号：
  OY2300000
• 海关编码：
  29322090
• 安全说明：
  S23,S25,S28,S28A
• 危险类别码：
  R20/21/22
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封保存，放置在通风、干燥的地方，避免与其它氧化物接触。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Isofraxidin
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 486-21-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 6,8-Dimethoxyumbelliferone
7-Hydroxy-6,8-dimethoxycoumarin
7-Hydroxy-6,8-dimethoxychromen-2-one
Formula : C11H10O5
Molecular Weight : 222,19 g/mol
CAS-No. : 486-21-5
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone] test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: crystalline
Colour: light yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 146 - 149 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 1,649
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

---

SECTION 16: Other information
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

生物活性

Isofraxidin 是一种源自刺五加（Acanthopanax senticosus）的香豆素成分，能够抑制 MMP-7 的表达和人肝癌细胞侵袭。此外，Isofraxidin 还通过抑制 ERK1/2 磷酸化作用于肝癌细胞，并减弱 iNOS 和 COX-2 表达。Isofraxidin 还能抑制 TLR4/髓样分化蛋白 2 (MD-2) 复合物的形成。

靶点

| COX-2 | TLR4 | MMP-7 |

体外研究

在肝癌细胞系中，Isofraxidin 在非毒性水平下通过抑制 ERK1/2 磷酸化来抑制 MMP-7 的表达和细胞侵袭。Isofraxidin 还能竞争性地抑制 TLR4/MD-2 复合物的形成，从而阻断 TLR4/NF-κB 信号传导途径。因此，Isofraxidin 具有潜在的治疗骨关节炎（OA）的作用。

化学性质

Isofraxidin 是一种白色结晶粉末，能溶于沸水，难溶于冷水，易溶于甲醇、乙醇和氢氧化钠溶液。它来源于肿节风、刺五加皮以及草珊瑚全株。

用途

异嗪皮啶具有抑菌消炎、抗肿瘤的作用，并可用于含量测定、鉴定及药理实验等。

反应信息

• 作为反应物：
  描述：

  异嗪皮啶 在 氢碘酸 作用下， 生成 6,7,8-trihydroxycoumarin
  参考文献：
  名称：

  Janot et al., Bulletin de la Societe de Chimie Biologique, 1955, vol. 37, p. 361,364

  摘要：

  DOI：
• 作为产物：
  描述：

  异嗪皮啶 7-O-beta-D-葡萄糖苷 在 硫酸 作用下， 以 水 为溶剂， 反应 1.0h， 以60 mg的产率得到异嗪皮啶
  参考文献：
  名称：

  Chemical studies of Coelopleurum gmelinii (D.C.) Ledeb. I. Constituents of the root.

  摘要：

  从根中分离出两种新香豆素（9 和 10）和一种新色酮（14），以及通过与真实样品比较而鉴定的八种已知香豆素（1-8）和三种已知色酮（11-13） Coelopleurum gmelinii (D.C.) LEDER（伞形科）。 9、10和14的结构确定为6-[(1R,2S)-1,3-二羟基-2-异戊酰氧基-3-甲基丁基]-7-甲氧基香豆素，6-[(1R,2S)-2-当归酰氧基-3-β-D-葡萄糖基氧基-1-羟基-3-甲基丁基]-7-甲氧基香豆素（叔-O-葡萄糖基当归醇A）和(S)-7-β-D-葡萄糖基氧基甲基-4-羟基-2-(分别为1-羟基-1-甲基乙基)-2, 3-二氢-5H-呋喃[3, 2-g] [1]苯并吡喃-5-酮(prim-O-葡萄糖基当归素)。

  DOI：

  10.1248/cpb.31.64

文献信息

• Synthetic Studies Directed Towards Various Homologues of Natural Sesquiterpene-Coumarin Ethers: The Domino Approach
  作者：Andrei Corbu、Juan M. Castro、Maurizio Aquino、Zoila Gandara、Pascal Retailleau、Siméon Arseniyadis

  DOI：10.1002/ejoc.200901352

  日期：2010.3

  A domino-based strategy was used to construct analogues containing the basic skeleton of the monocyclic sesquiterpene-coumarin ethers galbanic acid (1) and secodrial (3), through conversion of the domino adduct 19 into 10 and 11, chosen as representative targets. 1 H NMR patterns, corroborated by X-ray crystallographic analysis for two of the four possible diastereomeric arrangements of the six-membered

  通过将多米诺加合物 19 转化为 10 和 11，选择作为代表性目标，使用基于多米诺骨牌的策略来构建包含单环倍半萜烯-香豆素醚 galbanic 酸 (1) 和二元 (3) 基本骨架的类似物。已经确定了 1 H NMR 模式，通过 X 射线晶体学分析证实了各种 A-seco 萜烯共有的六元 B 环的四种可能非对映异构排列中的两种。观察到的趋势有助于设计取代基组合，为非对映体识别提供工具，这取决于相邻甲基的顺式/反式排列和采用的构象。
• Total Synthesis of Six 3,4-Unsubstituted Coumarins
  作者：Wenqing Gao、Qingyong Li、Jian Chen、Zhichao Wang、Changlong Hua

  DOI：10.3390/molecules181215613

  日期：——

  for the total synthesis of 3,4-unsubstituted coumarins from commercially available starting materials. Six examples were prepared, including five naturally occurring coumarins--7-hydroxy-6,8-dimethoxy-coumarin (isofraxidin), 7-hydroxy-6-methoxycoumarin (scopoletin), 6,7,8-trimethoxy-coumarin, 6,7-dimethoxycoumarin (scoparone), and 7,8-dihydroxycoumarin (daphnetin) and one synthetic coumarin, 7-hydr

  在本文中，我们描述了一种从市售原料中全合成 3,4-未取代香豆素的新方法。制备了六个实施例，包括五种天然存在的香豆素--7-羟基-6,8-二甲氧基-香豆素（isofraxidin）、7-羟基-6-甲氧基香豆素（东莨菪碱）、6,7,8-三甲氧基香豆素、6、 7-二甲氧基香豆素（scoparone）和7,8-二羟基香豆素（瑞香素）和一种合成香豆素，7-羟基-6-乙氧基香豆素。此外，还得到了五种重要的邻羟基苯甲醛中间体，即2,4-二羟基-3,5-二甲氧基苯甲醛、2,4-二羟基-5-甲氧基苯甲醛、5-乙氧基-2,4-二羟基-苯甲醛、2-羟基苯甲醛-3,4,5-三甲氧基苯甲醛和2-羟基-4,5-二甲氧基苯甲醛。本文开发的方法只涉及三到四个步骤，可以以极好的收率快速合成这些重要分子。这是 6,7,8-三甲氧基香豆素和 7-羟基-6-乙氧基香豆素的首次合成。
• Inhibitor for FcεRI expression on mast cell from Verbasucum thapsus L.
  作者：Satoru Tamura、Kunichika Yoshihira、Tomikazu Kawano、Nobutoshi Murakami

  DOI：10.1016/j.bmcl.2018.09.007

  日期：2018.11

  American medicinal plant, V. thapsus L., as a candidate of an anti-allergic lead which inhibits the expression of high-affinity receptor of IgE (FcεRI) on the surface of mast cells. Furthermore, the analysis of structure-activity relationship by using synthesized 2′,3′-dihydroxypuberulin analogs revealed that both hydroxy groups in the side chain and both of methyl moieties on phenolic hydroxy groups

  我们从南美药用​​植物V. thapsus L.中发现了2'，3'-二羟基青春素，作为抗过敏铅的候选物，该铅抑制了IgE（FcεRI）高亲和力受体在桅杆表面的表达细胞。此外，通过使用合成的2'，3'-二羟基青春粉蛋白类似物进行的结构-活性关系分析表明，侧链上的两个羟基以及酚羟基上的甲基均对有效活性至关重要，但C-的绝对构型3'的位置不是。公开了活性成分2'，3'-二羟基青春粉蛋白，其下调FcεRI的β链的mRNA水平，这与先前报道的降低γ链水平的活性天然产物不同。
• Horseradish peroxidase (HRP): a tool for catalyzing the formation of novel bicoumarins
  作者：Xiaoxv Gao、Shanshan Huang、Peipei Dong、Chao Wang、Jie Hou、Xiaokui Huo、Baojing Zhang、Tonghui Ma、Xiaochi Ma

  DOI：10.1039/c5cy01682g

  日期：——

  peroxidase (HRP) was used to effectively catalyze the dimerization of coumarins. On the basis of screening and preparative transformation, the catalytic ability of HRP to dimerize various coumarins was investigated. Coumarins that only had one substituted phenolic hydroxyl group could be selectively transformed into novel bicoumarins, while coumarins that had two or more hydroxyls could be transformed

  辣根过氧化物酶（HRP）用于有效催化香豆素的二聚化。在筛选和制备转化的基础上，研究了HRP对各种香豆素二聚的催化能力。仅具有一个取代酚羟基的香豆素可以选择性地转化为新型双香豆素，而具有两个或多个羟基的香豆素可以转化为多个双香豆素。获得了八种双香豆素，并通过光谱分析鉴定。其中，首次报道了双香豆素1b，2a，2b，3a和3b。还通过计算机研究了不同类型的香豆素与HRP之间的相互作用对接分析。使用转化产物作为标准物质，进行了催化反应的动力学分析。HRP催化香豆素二聚的最佳反应条件为1 g L -1 HRP，0.66 MH 2 O 2，pH 3、25°C和15分钟的孵育时间。双香豆素的产率为10％至40％，特别是双香豆素1a的产率为约35％。在体外生物测定中，几种新颖的双香豆素显示出潜在的α-葡萄糖苷酶抑制活性，可进一步用于开发抗糖尿病药。
• Natural and Unnatural A-<i>seco</i>Terpenes from Pulegone: Synthesis of Galbanic Acid and Marneral Revisited
  作者：Andrei Corbu、Maurizio Aquino、Manuel Perez、Zoila Gandara、Siméon Arseniyadis

  DOI：10.1002/ejoc.200901021

  日期：2009.12

  various A-seco terpenoids that have allowed us to prepare natural galbanic acid [(–)-1] from (S)-(–)-pulegone [(–)-2]. Furthermore, we were able to increase both the yield and step efficiency of the synthesis of marneral [(+)-7] as well as to access higher homologues of ent-galbanic acid [(+)-4], ent-secodrial [(+)-5], and bis-epi-secochiliotrin (6) from (R)-(+)-pulegone [(+)-2]. (© Wiley-VCH Verlag GmbH

  我们在此描述了一种改进的手性池策略，用于组装各种 A-seco 萜类化合物的核心结构 3（两个对映体），使我们能够从 (S)-(-)-胡薄荷[(-)-2]。此外，我们能够提高合成 [(+)-7] 的产量和步骤效率，以及获得 ent-galbanic 酸 [(+)-4]、ent-secodrial [( +)-5] 和来自 (R)-(+)-pulegone [(+)-2] 的双表皮环叶菊酯 (6)。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)