莽草酸

莽草酸 基本信息
CAS号 138-59-0 分子式 C7H10O5
分子量 174.15100 精确质量 　174.05300
PSA 　97.99000 LogP 　-1.51620
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等价的CAS号：

138-59-0,2306-23-2,10191-00-1,15271-51-9,16661-31-7,21967-35-1,90761-07-2
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目录
基本信息 制备方法与用途 物化性质 安全信息 合成路线 化学图谱 毒性 MSDS 结构与计算数据 上下游

基本信息 展开↓

CAS号：
138-59-0
3D弹球模型：
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分子式：
C7H10O5
分子量：
174.15100
中文名称：
莽草酸
英文名称：
Shikimic acid
中文别名：
莽草酸;
(3R,4S,5R)-(-)-3,4,5-三羟基-1-环己烯羧酸;
(3R,4S,5R)-(-)-3,4,5-三羟基-1-环己烯-1-甲酸
英文别名：
Shikimic acid;
(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid;
Shikimic Acid;
(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid;
(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid;
3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
精确分子量/精确质量：
174.05300
极性分子表面积/PSA：
97.99000
油水分配系数/LogP：

LogP值指的是某物质在正辛醇/水两相体系中的分配系数的对数值，反映了物质在油水两相中的分配情况。其中、LogP值越大，说明该物质越亲油；反之，LogP值越小，则说明该物质越亲水。
贝尔斯坦号/MDL：
MFCD00066278
EINECS：
205-334-2
PubChem：
24899647
BRN：
4782717
InChI：
InChI=1/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/p-1/t4-,5-,6-/m1/s1

生产制备方法及用途展开↓

制备方法

莽草酸是从中药八角茴香中提取的一种单体化合物。

合成制备方法

莽草酸是从中药八角茴香中提取的一种单体化合物。

用途简介

莽草酸通过影响花生四烯酸代谢，抑制血小板聚集，抑制动、静脉血栓及脑血栓形成，并具有有抗炎、镇痛作用，还可作为抗病毒和抗癌药物中间体。本品多用做制药中间体，具有一定刺激性，不宜直接使用。有机合成

用途

莽草酸通过影响花生四烯酸代谢，抑制血小板聚集，抑制动、静脉血栓及脑血栓形成，并具有有抗炎、镇痛作用，还可作为抗病毒和抗癌药物中间体。 本品多用做制药中间体，具有一定刺激性，不宜直接使用。

物化性质展开↓

外观与性状：
白色粉末
密度：
1.725 g/cm3
熔点：
185-187 °C(lit.)
沸点：
400.5ºC at 760 mmHg
闪点：
210.1ºC
水溶解性：
18 g/100 mL (20 ºC)
折射率：
-180 ° (C=1, H2O)
蒸汽压：
4.45E-08mmHg at 25°C
存储条件/存储方法：

应充氩气密封于阴凉干燥处保存。

稳定性相关：

1. 有吸湿性。能升华

2. 存在于烟叶中。

其它信息：

1. 性状：无色或白色针状结晶。

2. 溶解性：在20ºC水中溶解度为18%，微溶于乙醇、乙醚，几乎不溶于氯仿、苯。

3. 沸点（ºC）：400.5

4. 熔点（ºC）：185~187

5. 闪点（ºC）：210.1

6. 相对密度(d204)   ：1.725

安全信息展开↓

海关代码：
29181980
WGK_Germany：
3
德国有关水污染物质的分类清单
危险类别码：
R36/37/38
安全说明：
S22-S24/25
RTECS号：
GW4600000
安全标志：
S22:不要吸入粉尘。
S24/25:防止皮肤和眼睛接触。
危险标志：
Xi: Irritant;

合成路线查看所有的合成路线

  • 40983-58-2

    methyl 3,4,5-trihydroxycyclohexene-1-carboxylate

  • →

    ~99%

  • 138-59-0

    莽草酸

  • 91758-39-3

    91758-39-3

  • →

    ~88%

  • 138-59-0

    莽草酸

  • 1202183-69-4

    (1S,2R,6R)-4-(ethoxycarbonyl)-6-(4-nitrobenzoyloxy)-cyclohex-3-ene-1,2-diyl diacetate

  • →

    ~65%

  • 138-59-0

    莽草酸

化学图谱

  1. 莽草酸红外图谱(IR1)

  2. 莽草酸质谱(MS)

  3. 莽草酸核磁图(13CNMR)

  4. 莽草酸核磁图(1HNMR)

  5. 莽草酸红外图谱(IR2)

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毒理性展开↓

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GW4600000
CHEMICAL NAME :
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
CAS REGISTRY NUMBER :
138-59-0
LAST UPDATED :
199510
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C7-H10-O5
MOLECULAR WEIGHT :
174.17
WISWESSER LINE NOTATION :
L6UTJ AVQ CQ DQ EQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4000 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
Dominant lethal test
TYPE OF TEST :
Dominant lethal test

MUTATION DATA

TYPE OF TEST :
Morphological transformation
TEST SYSTEM :
Rodent - hamster Kidney
DOSE/DURATION :
250 mg/L
REFERENCE :
TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 19,43,1983 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 40,47,1986 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 40,47,1986 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,1171,1976
毒理学数据：

急性毒性数据：

小鼠腹腔LD：1mg/kg

致肿瘤数据：

小鼠经口TDLo：4000mg/kg

小鼠腹腔TDLo：400mg/kg

致突变数据：

小鼠腹腔显性致死试验：1000mg/kg

小鼠经口显性致死试验：3200mg/kg

仓鼠肾的形态转变试验：250mg/L

MSDS 展开↓

Name: Shikimic Acid 98% Material Safety Data Sheet
Synonym: 3,4,5-Trihydroxy-1-Cyclohexene-1-Carboxylic Acid
CAS: 138-59-0
Section 1 - Chemical Product   MSDS Name:Shikimic Acid 98% Material Safety Data Sheet
Synonym:3,4,5-Trihydroxy-1-Cyclohexene-1-Carboxylic Acid
Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
138-59-0 Shikimic Acid 98% 205-334-2
Hazard Symbols: None Listed.
Risk Phrases: None Listed.
Section 3 - HAZARDS IDENTIFICATION
  EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
Effects may be delayed. Substance may have carcinogenic potential.
Section 4 - FIRST AID MEASURES
  Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Section 5 - FIRE FIGHTING MEASURES
  General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use agent most appropriate to extinguish fire.
Section 6 - ACCIDENTAL RELEASE MEASURES
  General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.
Section 7 - HANDLING and STORAGE
  Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
  Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 138-59-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.
Section 9 - PHYSICAL AND CHEMICAL PROPERTIES
 
Physical State: Solid
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 185.00 - 187.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: 18g/100ml (20 c)
Specific Gravity/Density:
Molecular Formula: C7H10O5
Molecular Weight: 174.15
Section 10 - STABILITY AND REACTIVITY
  Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.
Section 11 - TOXICOLOGICAL INFORMATION
  RTECS#:
CAS# 138-59-0: GW4600000 LD50/LC50:
Not available.
Carcinogenicity:
Shikimic Acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.
Section 12 - ECOLOGICAL INFORMATION
 
Section 13 - DISPOSAL CONSIDERATIONS
  Dispose of in a manner consistent with federal, state, and local regulations.
Section 14 - TRANSPORT INFORMATION
 
IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.
Section 15 - REGULATORY INFORMATION
 
European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 138-59-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 138-59-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 138-59-0 is not listed on the TSCA inventory.
It is for research and development use only.

SECTION 16 - ADDITIONAL INFORMATION
N/A

分子结构与计算化学数据展开↓

分子结构数据

 

分子性质数据：

1、   摩尔折射率：38.14

2、   摩尔体积（cm3/mol）：100.9

3、   等张比容（90.2K）：331.7

4、   表面张力（3.0 dyne/cm）：116.6

5、   极化率（0.5 10-24cm3）：15.12

计算化学数据

1、   疏水参数计算参考值（XlogP）：-1.7

2、   氢键供体数量：4

3、   氢键受体数量：5

4、   可旋转化学键数量：1

5、   互变异构体数量：

6、   拓扑分子极性表面积（TPSA）：98

7、   重原子数量：12

8、   表面电荷：0

9、   复杂度：222

10、同位素原子数量：0

11、确定原子立构中心数量：3

12、不确定原子立构中心数量：0

13、确定化学键立构中心数量：0

14、不确定化学键立构中心数量：0

15、共价键单元数量：1

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