5,7-二甲氧基香豆素 | 487-06-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 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: 5,7-二甲氧基香豆素
• 中文别名: 5,7-二甲氧香豆素；柠美内酯；白檬素；5,7-二甲氧基香豆素(Citropten)
• 英文名称: Limettin
• 英文别名: 5,7-dimethoxycoumarin；citropten；5,7-dimethoxy-2H-chromen-2-one；5,7-dimethoxy-2H-1-benzopyran-2-one；5,7-dimethoxychromen-2-one
• CAS: 487-06-9
• 化学式: C₁₁H₁₀O₄
• mdl: MFCD00006870
• 分子量: 206.198
• InChiKey: NXJCRELRQHZBQA-UHFFFAOYSA-N

物化性质

• 熔点：
  146-149 °C (lit.)
• 沸点：
  305.04°C (rough estimate)
• 密度：
  1.2607 (rough estimate)
• 溶解度：
  可溶于乙腈（少许）、氯仿（少许）
• LogP：
  1.891 (est)
• 物理描述：
  Solid
• 碰撞截面：
  138.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
• 保留指数：
  1916;1916
• 稳定性/保质期：
  按照规定使用和储存，不会发生分解，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S36/37
• 危险类别码：
  R43
• WGK Germany：
  3
• RTECS号：
  GN6530000
• 危险标志：
  GHS07
• 危险性描述：
  H317
• 危险性防范说明：
  P280
• 储存条件：
  温度：2-8°C 储存方式：密封保存，放置于通风、干燥处。目前暂无其他存储建议。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 5,7-Dimethoxycoumarin
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. : 487-06-9
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
Classification according to Regulation (EC) No 1272/2008
Skin sensitisation (Category 1), H317
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xi Irritant R43
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H317 May cause an allergic skin reaction.
Precautionary statement(s)
P280 Wear protective gloves.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : Citropten
Limettin
Formula : C11H10O4
Molecular Weight : 206,19 g/mol
CAS-No. : 487-06-9
EC-No. : 207-646-4
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
5,7-Dimethoxy-2-benzopyrone
CAS-No. 487-06-9 Skin Sens. 1; H317 <= 100 %
EC-No. 207-646-4
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
5,7-Dimethoxy-2-benzopyrone
CAS-No. 487-06-9 Xi, R43 <= 100 %
EC-No. 207-646-4
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
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. Consult a physician.
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. 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
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
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.
Specific end use(s)
A part 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
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses 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.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 146 - 149 °C - lit.
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- no data available
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
Other decomposition products - no data available
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
Germ cell mutagenicity
Human
lymphocyte
Sister chromatid exchange
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
photosensitivity, 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. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Citropten（5,7-二甲氧基香豆素）是从佛手柑油中分离出的一种香豆素，对A2058人黑色素瘤细胞株表现出抗增殖活性。

化学性质

Citropten是一种白色结晶粉末，可溶于甲醇、乙醇和DMSO等有机溶剂。它来源于佛手。

用途

5,7-二甲氧基香豆素具有抗急性肾功能衰竭的作用。

反应信息

• 作为反应物：
  描述：

  5,7-二甲氧基香豆素 在 sodium hydroxide 作用下， 生成 白蜡树精
  参考文献：
  名称：

  Bhavsar; Desai, Indian Journal of Pharmacy, 1951, vol. 13, p. 200,203

  摘要：

  DOI：
• 作为产物：
  描述：

  2-formyl-3,5-dimethoxyphenyl 2-chloroacetate 以 N,N-二甲基甲酰胺 为溶剂， 以35%的产率得到5,7-二甲氧基香豆素
  参考文献：
  名称：

  在银阴极还原取代的 2-氯乙酸苯酯：香豆素的电合成

  摘要：

  To explore the electrosynthesis of coumarins, cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the reduction of the carbon-chlorine bond of five substituted phenyl 2-chloroacetates at silver cathodes in dimethylformamide (DMF) containing 0.10 M tetra-n-butylammonium tetrafluoroborate (TBABF(4)) as supporting electrolyte; the five substrates are 2-formylphenyl 2-chloroacetate (1a), 2-acetylphenyl 2-chloroacetate (2a), methyl 2-(2-chloroacetoxy)benzoate (3a), 2-formyl-5-methoxyphenyl 2-chloroacetate (4a), and 2-formyl-3,5-dimethoxyphenyl 2-chloroacetate (5a). We have examined (a) the effects of substituents on the benzene ring of the substrate as well as the nature of the aryl carbonyl moiety on the formation of the coumarin product and (b) the effect of solvent-namely, DMF, acetonitrile (CH3CN), benzonitrile (PhCN), and propylene carbonate (PC)-and substrate concentration on the yield of the coumarin. It was found that the most unsubstituted substrate (1a) afforded the highest yield (41%) of the desired coumarin in a DMF-TBABF(4) medium. A mechanistic scheme is proposed to account for the formation of the coumarin. Furthermore, the only other products seen in these reductions are 2-substituted phenols, which are precursors for synthesis of the various substrates. (C) 2014 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.0551412jes

文献信息

• Pd^II-Catalyzed Reaction of Phenols with Propiolic Esters. A Single-Step Synthesis of Coumarins
  作者：Tsugio Kitamura、Kiyomi Yamamoto、Masashi Kotani、Juzo Oyamada、Chengguo Jia、Yuzo Fujiwara

  DOI：10.1246/bcsj.76.1889

  日期：2003.10

  The intermolecular reaction of phenols with propiolic esters in TFA in the presence of a Pd(OAc)2 catalyst, affording coumarin derivatives, is described. An exclusive formation of 5,6,7-trimethoxy-...

  描述了在 Pd(OAc)2 催化剂存在下，苯酚与丙炔酸酯在 TFA 中的分子间反应，得到香豆素衍生物。5,6,7-三甲氧基-...
• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。
• Direct Synthesis of Coumarins by Pd(II)-Catalyzed Reaction of Alkoxyphenols and Alkynoates
  作者：Juzo Oyamada、Chengguo Jia、Yuzo Fujiwara、Tsugio Kitamura

  DOI：10.1246/cl.2002.380

  日期：2002.3

  Reaction of alkoxyphenols and alkynoates in the presence of a catalytic amount of Pd(OAc)2 in trifluoroacetic acid at room temperature gave coumarin derivatives in high yields. This procedure provides a convenient method for direct synthesis of coumarin derivatives under very mild conditions.

  在催化量的 Pd(OAc) 2 在三氟乙酸中的存在下，烷氧基苯酚和炔酸酯在室温下反应以高产率得到香豆素衍生物。该程序为在非常温和的条件下直接合成香豆素衍生物提供了一种方便的方法。
• Cascade Synthesis of 3-Alkenylcoumarins by Palladium-catalyzed Reaction of Phenols and Ethyl Propiolate
  作者：Tsugio Kitamura、Kotaro Tatemoto、Mariko Sakai、Juzo Oyamada

  DOI：10.1246/cl.2012.705

  日期：2012.7.5

  A highly effective cascade process giving 3-alkenylcoumarins is furnished by a series of reactions involving pallada-arylation of ethyl propiolate with phenols, intramolecular transesterification t...

  提供 3-烯基香豆素的高效级联过程是通过一系列反应提供的，包括丙炔酸乙酯与苯酚的钯芳基化、分子内酯交换...
• Total Synthesis of (±)–Exotine B
  作者：Bichu Cheng、Giulio Volpin、Johannes Morstein、Dirk Trauner

  DOI：10.1021/acs.orglett.8b01817

  日期：2018.7.20

  heterodimeric indole/coumarin natural product exotine B was synthesized for the first time. The carbon skeleton of the natural product was formed rapidly by a palladium-catalyzed Suzuki cross-coupling reaction and a gallium-catalyzed three-component [4 + 3] cycloaddition reaction. An alternative biosynthesis of exotine B is proposed based on the total synthesis. Improved syntheses of coumarin natural products

  首次合成了异二聚吲哚/香豆素天然产物外泌素B。天然产物的碳骨架通过钯催化的Suzuki交叉偶联反应和镓催化的三组分[4 + 3]环加成反应迅速形成。在总合成的基础上，提出了外泌素B的另一种生物合成方法。还报道了香豆素天然产物亚麻二烯和香豆素的合成得到改善。

表征谱图