(R)-(+)-苹果酸二异丙酯 | 83540-97-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: (R)-(+)-苹果酸二异丙酯
• 中文别名: D-苹果酸二异丙酯；苹果酸二异丙酯
• 英文名称: (2R)-diisopropyl 2-hydroxybutanedioate
• 英文别名: diisopropyl (R)-2-hydroxy-succinate；diisopropyl (R)-(+)-malate；diisopropyl malate；(R)-D-diisopropyl malate；diisopropyl (R)-Malate；D-diisopropyl malate；dipropan-2-yl (2R)-2-hydroxybutanedioate
• CAS: 83540-97-0
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: XYVHRFVONMVDGK-MRVPVSSYSA-N

物化性质

• 沸点：
  237 °C(lit.)
• 密度：
  1.055 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  避免使用强氧化剂

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2918199090
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Diisopropyl (R)-(+)-malate
CAS-No. : 83540-97-0
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 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C10H18O5
Molecular Weight : 218,25 g/mol
Component Concentration
Diisopropyl (R)-(+)-malate
CAS-No. 83540-97-0 -

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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
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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 breathing vapors, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. 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 inhalation of vapour or mist.
Normal measures for preventive fire protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
no data available

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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
Safety glasses with side-shields conforming to EN166 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
Impervious clothing., The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
Colour: colourless
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 237 °C - lit.
boiling range
g) Flash point 113 °C - closed cup
h) Evaporation 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 1,055 g/cm3 at 25 °C
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
no data available
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

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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 sensitization
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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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
no data available
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. Contact a licensed
professional waste disposal service to dispose of this material.
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

反应信息

• 作为反应物：
  描述：

  (R)-(+)-苹果酸二异丙酯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 生成 2R-hydroxy-3S-(phenylmethyl)butanedioic acid
  参考文献：
  名称：

  Process and intermediates for isopropyl 3S-amino-2R-hydroxy-alkanoates

  摘要：

  从R-苹果酸制备异丙基3S-氨基-4-环己基-2R-羟基丁酸酯和3S-氨基-2R-羟基-5-甲基己酸酯的过程和中间体。这些产品在合成某些肾素抑制剂中已知具有实用性。

  公开号：

  US04965372A1
• 作为产物：
  描述：

  L-(+)-酒石酸二异丙酯 在 samarium diiodide 、 乙二醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以99%的产率得到(R)-(+)-苹果酸二异丙酯
  参考文献：
  名称：

  通过SmI 2诱导的电子转移过程对α-氧化酯进行高效脱氧

  摘要：

  在室温下，很容易将各种α-氧化酯，例如α-乙酰氧基-，α-甲氧基-，α-OTHP和α-羟基酯还原，以良好的收率获得优良的收率的相应饱和酯。有效的电子转移系统SmI 2 -THF-HMPA。该方法已成功地应用于酒石酸（R，R）到苹果酸（R）的直接转化。

  DOI：

  10.1016/s0040-4039(00)99165-2

文献信息

• [EN] N-HYDROXYAMIDE DERIVATIVES AND USE THEREOF<br/>[FR] DERIVES N-HYDROXYAMIDE ET LEUR APPLICATION
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2006010751A1

  公开（公告）日：2006-02-02

  The present invention is related to N-hydroxyamide derivatives of Formula (I) and use thereof, in particular for the treatment and/or prophylaxis of autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, cancer, respiratory diseases and fibrosis, including multiple sclerosis, arthritis, emphysema, chronic obstructive pulmonary disease, liver and pulmonary fibrosis.

  本发明涉及式（I）的N-羟基酰胺衍生物及其用途，特别是用于治疗和/或预防自身免疫性疾病、炎症性疾病、心血管疾病、神经退行性疾病、癌症、呼吸道疾病和纤维化，包括多发性硬化症、关节炎、肺气肿、慢性阻塞性肺病、肝脏和肺部纤维化。
• Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives
  作者：Steven V. Ley、Elena Diez、Darren J. Dixon、Richard T. Guy、Patrick Michel、Gillian L. Nattrass、Tom D. Sheppard

  DOI：10.1039/b412788a

  日期：——

  The preparation of butane-2,3-diacetal protected glycolic acid and related systems is described together with highly selective alkylation reactions of (R,R) and (S,S) butanediacetal protected glycolic acid. These compounds are readily deprotected to give enantiopure alpha-hydroxyacids, alpha-hydroxyesters or alpha-hydroxyamides by suitable choice of conditions.

  描述了由2,3-二缩醛丁烷保护的乙醇酸的制备方法和相关系统，以及（R，R）和（S，S）丁二缩醛保护的乙醇酸的高度选择性烷基化反应。这些化合物可容易地脱保护，得到对映体纯的α-羟基酸，由条件适当选择的α-羟基酯或α-羟基酰胺。
• Concise Route to the Chiral Pyrrolidine Core of Selective Inhibitors of Neuronal Nitric Oxide
  作者：Fengtian Xue、Wenxin Gu、Richard B. Silverman

  DOI：10.1021/ol902109t

  日期：2009.11.19

  2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine (2), a key intermediate for the preparation of novel neuronal nitric oxide synthase (nNOS) inhibitors, is synthesized using diisopropyl (R)-(+)-malate as the starting material. The key steps involve a Frater−Seebach diastereoselective alkylation and a fast intramolecular cyclization.

  2-(((3 R ,4 R )-4-(烯丙氧基)-1-苄基吡咯烷-3-基)甲基)-6-(2,5-二甲基-1H-吡咯-1-基)-4-甲基吡啶 ( 2 ) 是制备新型神经元一氧化氮合酶 (nNOS) 抑制剂的关键中间体，它是以 ( R )-(+)-苹果酸二异丙酯为起始原料合成的。关键步骤包括 Frater-Seebach 非对映选择性烷基化和快速分子内环化。
• [EN] TOPICAL COMPOSITIONS CONTAINING SYNTHETIC ESTERS OF SINAPINIC ACID AND METHODS FOR TREATING KERATIN SURFACES<br/>[FR] COMPOSITIONS TOPIQUES CONTENANT DES ESTERS SYNTHÉTIQUES D'ACIDE SINAPINIQUE ET PROCÉDÉS DE TRAITEMENT DE SURFACES DE KÉRATINE
  申请人：ELC MAN LLC

  公开号：WO2018165189A1

  公开（公告）日：2018-09-13

  A topical composition comprising a synthetic compound that is an ester of sinapinic acid, a method for treating skin to provide one or more benefits selected from (a) protecting against UV radiation, (b) inhibiting DNA damage in skin cells, (c) inhibiting skin inflammation, and (d) scavenging free radicals by topically applying a composition containing the synthetic compound and a method for synthesizing the compound.

  一种含有合成的辛太尼酸酯化合物的局部组成物，用于治疗皮肤，提供以下一种或多种益处：(a)保护免受紫外线辐射的伤害，(b)抑制皮肤细胞的DNA损伤，(c)抑制皮肤炎症，(d)通过局部应用含有合成化合物的组成物清除自由基，并提供一种合成该化合物的方法。
• N-Hydroxyamide Derivatives and Use Thereof
  申请人：Swinnen Dominique

  公开号：US20080021028A1

  公开（公告）日：2008-01-24

  The present invention is related to N-hydroxyamide derivatives of Formula (I) and use thereof, in particular for the treatment and/or prophylaxis of autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, cancer, respiratory diseases and fibrosis, including multiple sclerosis, arthritis, emphysema, chronic obstructive pulmonary disease, liver and pulmonary fibrosis.

  本发明涉及公式（I）的N-羟基酰胺衍生物及其用途，特别用于治疗和/或预防自身免疫性疾病、炎症性疾病、心血管疾病、神经退行性疾病、癌症、呼吸系统疾病和纤维化，包括多发性硬化症、关节炎、肺气肿、慢性阻塞性肺疾病、肝脏和肺纤维化。