藏红花酸 | 27876-94-4

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 藏红花酸
• 中文别名: TRANS-藏花酸；臧红花酸；蕃紅[花]酸
• 英文名称: crocetin
• 英文别名: trans-crocetin；α-crocetin；all-trans-crocetin；(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid
• CAS: 27876-94-4；8022-19-3
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: PANKHBYNKQNAHN-MQQNZMFNSA-N

物化性质

• 熔点：
  285°
• 沸点：
  386.14°C (rough estimate)
• 密度：
  1.0786 (rough estimate)
• 溶解度：
  DMSO（微溶，加热）、甲醇（微溶）
• LogP：
  4.312 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

毒理性

• 相互作用

藏红花柱头成分 safranal 和 crocin 的抗惊厥活性在小鼠的戊四唑 (PTZ) 诱导的惊厥模型中进行了评估。Safranal（0.15和0.35 mL/kg，i.p.）减少了惊厥持续时间，延迟了强直性惊厥的发作，并保护小鼠免于死亡。Crocin（200 mg/kg，i.p.）没有显示出抗惊厥活性。/Safranal 和 crocin/

The anticonvulsant activities of Crocus sativus stigma constituents, safranal and crocin, were evaluated in mice using pentylenetetrazole (PTZ)-induced convulsions in mice. Safranal (0.15 and 0.35 mL/kg, i.p.) reduced the seizure duration, delayed the onset of tonic convulsions and protected mice from death. Crocin (200 mg/kg, i.p.) did not show anticonvulsant activity. /Safranal and crocin/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

红花雄蕊的50%乙醇提取物，以每千克体重125-250.0毫克的剂量进行胃内给药，在小鼠中具有镇静作用，并且增强了巴比妥类药物的镇静效果。/藏红花雄蕊的乙醇提取物/

Intragastric administration of 125-250.0 mg/kg body weight (bw) of a 50% ethanol extract of the stigmas had a tranquillizing effect in mice, and potentiated the sedative effects of barbiturates. /Ethanol extract of Stigma Croci/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

以95%乙醇提取的藏红花柱头应用于小鼠皮肤，剂量为100 mg/kg体重，能够抑制皮肤肿瘤发生的启动和促进阶段，推迟乳头状瘤形成的时间，并减少每只小鼠的平均乳头状瘤数量。每天通过灌胃给予相同提取物的剂量为100.0 mg/kg体重，持续30天，能够减少由20-甲基胆蒽诱导的小鼠软组织肉瘤发生率10%。将藏红花柱头的乙醇提取物通过灌胃给予小鼠，剂量为100.0 mg/kg体重，能够分别抑制固体达尔顿淋巴瘤腹水和肉瘤180肿瘤的生长87%和41%。每周皮下注射藏红花素400.0 mg/kg体重，持续13周，能够减缓结肠腺癌的生长，并延长雌性小鼠的寿命，但对雄性小鼠无效。/藏红花柱头乙醇提取物/

Topical application of 100 mg/kg bw of a 95% ethanol extract of the stigmas inhibited two-stage initiation and promotion of skin carcinogenesis in mice, delaying the onset of papilloma formation and reducing the mean number of papillomas per mouse. Intragastric administration of 100.0 mg/kg bw of the same extract per day for 30 days reduced the incidence of soft tissue sarcomas induced by 20-methylcholanthrene by 10% in mice. Intragastric administration of 100.0 mg/kg bw of an ethanol extract of the stigmas to mice inhibited the growth of solid Dalton lymphoma ascites and sarcoma 180 tumors by 87% and 41%, respectively. Subcutaneous administration of 400.0 mg/kg bw of crocin weekly for 13 weeks, slowed the growth of colon adenocarcinoma and increased the lifespan of female but not male mice. /Ethanol extract of Stigma Croci/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

腹腔注射50毫克/千克体重的95%乙醇番红花雄蕊提取物给小鼠，部分防止了顺铂治疗引起的体重下降、血红蛋白水平降低和白细胞计数减少。/藏红花雄蕊乙醇提取物/

Intraperitoneal administration of 50 mg/kg bw of a 95% ethanol extract of the stigmas to mice partially prevented the decreases in body weight, hemoglobin levels and leukocyte counts caused by cisplatin treatments. /Ethanol extract of Stigma croci/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者向前倾或将其置于左侧（如果可能的话，头部向下），以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 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. Chemical Product and Company Identification
Saffron
Common Name/
Trade Name
Manufacturer
Commercial Name(s)
Synonym
Chemical Name
Chemical Family
Saffron

---

Section 4. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for
at least 15 minutes. Get medical attention if irritation occurs.
Skin Contact Wash with soap and water. Get medical attention if irritation develops.
Serious Skin Contact Not available.
Inhalation If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Get medical attention.
Serious Inhalation Not available.
Ingestion Do NOT induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an
unconscious person. If large quantities of this material are swallowed, call a physician immediately. Loosen
tight clothing such as a collar, tie, belt or waistband.
Serious Ingestion Not available.

---

Section 5. Fire and Explosion Data
Flammability of the Product May be combustible at high temperature.
Auto-Ignition Temperature Not available.
Not available.
Flash Points
Not available.
Flammable Limits
Products of Combustion These products are carbon oxides (CO, CO2).
Fire Hazards in Presence of Slightly flammable to flammable in presence of heat.
Various Substances
Explosion Hazards in Presence Risks of explosion of the product in presence of mechanical impact: Not available.
of Various Substances Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
and Instructions LARGE FIRE: Use water spray, fog or foam. Do not use water jet.
Not available.
Special Remarks on
Fire Hazards
Special Remarks on Explosion Not available.
Hazards

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Section 6. Accidental Release Measures
Small Spill Use appropriate tools to put the spilled solid in a convenient waste disposal container. Finish cleaning by
spreading water on the contaminated surface and dispose of according to local and regional authority
requirements.
Large Spill Use a shovel to put the material into a convenient waste disposal container. Finish cleaning by spreading
water on the contaminated surface and allow to evacuate through the sanitary system.

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Section 7. Handling and Storage
Precautions Keep away from heat. Keep away from sources of ignition. Ground all equipment containing material. Do not
breathe dust.
Storage Keep container tightly closed. Keep container in a cool, well-ventilated area.
Saffron

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Section 8. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep
exposure to airborne contaminants below the exposure limit.
Personal Protection Safety glasses. Synthetic apron. Gloves (impervious).
Personal Protection in Case of Splash goggles. Full suit. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
a Large Spill specialist BEFORE handling this product.
Exposure Limits Not available.

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Section 9. Physical and Chemical Properties
Physical state and appearance Solid. (Fibers) Odor Not available.
Taste Not available.
Molecular Weight 328.39 g/mole
Color Red-Yellow
pH (1% soln/water) Not available.
Boiling Point Not available.
Melting Point Decomposes.
Not available.
Critical Temperature
Specific Gravity Not available.
Vapor Pressure Not applicable.
Vapor Density Not available.
Volatility Not available.
Odor Threshold Not available.
Water/Oil Dist. Coeff. Not available.
Not available.
Ionicity (in Water)
Dispersion Properties Not available.
Solubility Not available.

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Section 10. Stability and Reactivity Data
The product is stable.
Stability
Instability Temperature Not available.
Conditions of Instability Excess heat
Incompatibility with various Not available.
substances
Non-corrosive in presence of glass.
Corrosivity
Special Remarks on Not available.
Reactivity
Not available.
Special Remarks on
Corrosivity
Polymerization Will not occur.
Saffron

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Section 11. Toxicological Information
Routes of Entry Inhalation. Ingestion.
Toxicity to Animals LD50: Not available.
LC50: Not available.
Chronic Effects on Humans Not available.
Other Toxic Effects on
Slightly hazardous in case of ingestion.
Humans Non-irritant for skin. Non-hazardous in case of inhalation.
Special Remarks on Not available.
Toxicity to Animals
Special Remarks on Not available.
Chronic Effects on Humans
Special Remarks on other Acute Potential Health Effects:
Toxic Effects on Humans Not lilkely to cause eye, skin, or respiratory tract irritation.
Ingestion: expected to be a slight or low hazard.

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Section 12. Ecological Information
Ecotoxicity Not available.
BOD5 and COD Not available.
Products of Biodegradation Possibly hazardous short term degradation products are not likely. However, long term degradation products
may arise.
Toxicity of the Products The product itself and its products of degradation are not toxic.
of Biodegradation
Special Remarks on the Not available.
Products of Biodegradation

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Section 13. Disposal Considerations
Waste Disposal Waste must be disposed of in accordance with federal, state and local environmental
control regulations.

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Section 14. Transport Information
DOT Classification Not a DOT controlled material (United States).
Identification Not applicable.
Special Provisions for Not applicable.
Transport
DOT (Pictograms)

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Section 15. Other Regulatory Information and Pictograms
Federal and State No products were found.
Regulations
California California prop. 65: This product contains the following ingredients for which the State of California has
found to cause cancer which would require a warning under the statute: No products were found.
Proposition 65
Warnings
California prop. 65: This product contains the following ingredients for which the State of California has
found to cause birth defects which would require a warning under the statute: No products were found.
Saffron
Other Regulations Not available.
WHMIS (Canada) Not controlled under WHMIS (Canada).
Other Classifications
DSCL (EEC) This product is not classified Not applicable.
according to the EU regulations.
Health Hazard
HMIS (U.S.A.) 1 National Fire Protection
1 Flammability
1 Association (U.S.A.)
Fire Hazard
1 0 Reactivity
Health
Reactivity
0
Specific hazard
Personal Protection
C
WHMIS (Canada)
(Pictograms)
DSCL (Europe)
(Pictograms)
TDG (Canada)
(Pictograms)
ADR (Europe)
(Pictograms)
Protective Equipment
Gloves (impervious).
Synthetic apron.
Not applicable.
Safety glasses.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

蕃紅[花]酸又名藏红花酸。这是一种水溶性的类胡萝卜素，存在于藏红花和栀子中。它不仅是藏红花的主要成分，还具有抗癌、抑制肿瘤、降血脂、护肝、淬灭自由基、抗氧化等多种功效。此外，其水溶性好、着色力强，并能在pH值为1～4范围内均呈现鲜艳的金黄色，一旦着色非常稳定，因此广泛应用于医药和食品领域。

生物活性

Transcrocetin 是从藏红花中提取的一种可以透过血脑屏障并具有高亲和力NMDA受体拮抗作用的化合物。

靶点

Human Endogenous Metabolite (人体内源性代谢物)

体外研究

Transcrocetin（顺-藏红花酸），一种源自crocin apocarotenoids的番紅[花]酸代谢物，已被证明具有很强的NMDA受体亲和力，并被认为是藏红花神经系统活性的原因之一。为确保Caco-2细胞在整个运输实验中保持不变的活力，在添加测试化合物后的24小时，通过MTT试验测量了细胞线粒体脱氢酶活性：含乙醇提取物的藏红花（SE，0.5-1 mg/mL）和crocin-1（250-1000 µM），未观察到显著的变化。在Transcrocetin 10 µM水平下，细胞活力无变化；而更高浓度（40-160 µM）则显著降低了细胞活力。

化学性质

藏红花酸是一种黄色结晶粉末，可溶于甲醇、乙醇和DMSO等有机溶剂。它来源于栀子、西红花及鸢尾科番红花属的藏红花柱头和藏红花。

用途

藏红花酸具有抗肿瘤、抗动脉粥样硬化、抗高血压及治疗出血性休克、抗氧化、保肝利胆等多种功效。

反应信息

• 作为反应物：
  描述：

  藏红花酸 在 二乙胺基三氟化硫 作用下， 以 乙醚 为溶剂， 反应 2.67h， 生成
  参考文献：
  名称：

  西红花酸单葡萄糖醛酸的合成方法

  摘要：

  本发明涉及一种体内代谢产物的合成方法。该方法包括如下步骤：从中药栀子中提取分离得西红花苷，并将西红花苷水解成西红花酸，以西红花酸为底物合成西红花酸的氟代物，并用氟代物与D‑葡萄糖醛酸反应生成目标化合物‑西红花酸单葡萄糖醛酸。该合成方法原理简单，操作方便，对设备要求低，可以广泛推广应用。

  公开号：

  CN108864216A
• 作为产物：
  描述：

  栀子黄 在 potassium hydroxide 作用下， 生成 藏红花酸
  参考文献：
  名称：

  Effects of Intestinal Microbiota on Pharmacokinetics of Crocin and Crocetin in Male Sprague-Dawley Rats

  摘要：

  除了肝代谢外，肠道微生物在药物代谢中的作用被认为在异物生物转化中是重要的。藏红花素及其去糖苷基形式藏红花酸，从许多植物中分离出来，包括藏红花的干柱和栀子花果实，已被用于治疗炎症、癌症和代谢紊乱。在这项研究中，通过给予预先用头孢氨苄、土霉素和红霉素等抗生素混合物进行为期三天的连续处理的雄性大鼠单次口服600毫克/千克藏红花，研究了肠道微生物对藏红花药代动力学的影响。在藏红花处理后，通过LC-MS收集血液、尿液和粪便，评估藏红花和藏红花酸的药代动力学特性。结果表明，与藏红花酸相比，藏红花的肠道吸收相对较少，而藏红花通过肠道微生物代谢为藏红花酸可能是吸收的关键步骤。目前的结果清楚地表明，藏红花的体内药理作用可能主要是由其去糖苷基形式藏红花酸产生的作用，而肠道微生物对糖苷类天然产物的代谢应被考虑以了解它们的药效作用。

  DOI：

  10.3390/metabo10110424

文献信息

• 3-FURYL-2-CYANO-2-ACRYLAMIDE DERIVATIVE, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION AND USE THEREOF
  申请人：JENKEM TECHNOLOGY CO., LTD. (BEIJING)

  公开号：US20160272604A1

  公开（公告）日：2016-09-22

  Disclosed are a 3-furyl-2-cyano-2-acrylamide derivative with epidermal growth factor receptor (EGFR) inhibitory activity and pharmaceutical acceptable salt thereof, together with preparation method thereof, pharmaceutical composition comprising the compound, and application of the compound in treating senile dementia (AD). The new compound is shown as formula I, wherein R 1 is selected from the group consisting of H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl and C 3 -C 6 cycloalkyl; R 2 is selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl and heteroaralkyl; X is selected from the group consisting of CH 2 , NH, O and S; m and n are all integers greater than or equal to zero.

  揭示了一种具有表皮生长因子受体（EGFR）抑制活性的3-呋喃基-2-氰基-2-丙烯酰胺衍生物及其药用可接受盐，以及其制备方法，包含该化合物的药物组合物，以及该化合物在治疗老年性痴呆症（AD）中的应用。新化合物的化学式如下，其中R1选自H、C1-C6烷基、C2-C6烯基、C2-C6炔基和C3-C6环烷基组成的群；R2选自烷基、环烷基、烯基、炔基、芳基、杂芳基、芳基烷基和杂芳基烷基组成的群；X选自CH2、NH、O和S组成的群；m和n均为大于或等于零的整数。
• [EN] BIPOLAR TRANS CAROTENOID SALTS AND THEIR USES<br/>[FR] SELS DE CAROTENOIDES TRANS BIPOLAIRES ET LEURS UTILISATIONS
  申请人：DIFFUSION PHARMACEUTICALS LLC

  公开号：WO2005028411A1

  公开（公告）日：2005-03-31

  The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.

  这项发明涉及转型类胡萝卜素盐化合物，制备它们的方法，溶解它们的方法以及它们的用途。这些化合物在改善氧气在包括人类在内的哺乳动物的红细胞和体组织之间的扩散性方面是有用的。
• Cyclothiocarbamate derivatives as progesterone receptor modulators and methods of treating skin disorders
  申请人：Wyeth

  公开号：US20040014798A1

  公开（公告）日：2004-01-22

  The present invention provides methods of treating skin disorders includes delivering to a mammal a composition containing a compound of formula I, or tautomers thereof, in a regimen, wherein formula I is: 1 and wherein R 1 -R 5 and Q 1 are defined as described herein. Specifically, methods for treating acne, hirsutism, and conditioning the skin are described. Also provided are novel PR modulators of formula II.

  本发明提供了治疗皮肤疾病的方法，包括向哺乳动物输送含有式I化合物或其互变异构体的组合物，其中式I为： 1 其中R 1 -R 5 和Q 1 如本文所述。具体描述了治疗痤疮、多毛症和调理皮肤的方法。还提供了式II的新型PR调节剂。
• POLYMER-CARBOHYDRATE CONJUGATES FOR DRUG DELIVERY TECHNOLOGY
  申请人：Wu Nian

  公开号：US20150157721A1

  公开（公告）日：2015-06-11

  The invention comprises compounds, methods of making, and methods of using. The compounds may have a linear or cylic backbone and three or four appended functional groups: one or two lipohilic compounds including sterols or “fat soluble” vitamins, one or two hydrophilic polymer, and one or two carbohydrate. A group of polymer-carbohydrate conjugates having a central backbone and three appended functional groups are disclosed wherein one lipophilic compound is void of both steroid acids. The conjugate may have fatty acids as the primary lipophilic carrier, one hydrophilic polymer, and one carbohydrate. Specific functional groups may be selected for specific applications in formulating pharmaceuticals, cosmetics, nutriceuticals, and the like. Typical coupling reaction of the conjugates may involve one or more or combinations or in series of alkylation including N-alkylation or O-alkylation, etherification, esterification and amidation chemical processes. A variety of linkers between the backbone and functional groups may also be selected to modify the carriers or center backbones for the coupling reactions and optimize performance of the conjugates.

  该发明包括化合物、制备方法和使用方法。这些化合物可能具有线性或环状的骨架，以及三个或四个附加的功能基团：一个或两个疏水化合物，包括固醇或“脂溶性”维生素，一个或两个亲水性聚合物，以及一个或两个碳水化合物。公开了一组具有中心骨架和三个附加功能基团的聚合物-碳水化合物共轭物，其中一个疏水性化合物不含类固醇酸。该共轭物可能以脂肪酸作为主要疏水载体，一个亲水性聚合物和一个碳水化合物。特定的功能基团可以根据在制备药物、化妆品、营养保健品等方面的具体应用而选择。共轭物的典型偶联反应可能涉及一种或多种或组合或串联的烷基化，包括N-烷基化或O-烷基化，醚化，酯化和酰胺化化学过程。还可以选择各种连接剂连接骨架和功能基团之间，以修改载体或中心骨架以进行偶联反应并优化共轭物的性能。
• Characterization of the Saffron Derivative Crocetin as an Inhibitor of Human Lactate Dehydrogenase 5 in the Antiglycolytic Approach against Cancer
  作者：Carlotta Granchi、Serena Fortunato、Serena Meini、Flavio Rizzolio、Isabella Caligiuri、Tiziano Tuccinardi、Hyang Yeon Lee、Paul J. Hergenrother、Filippo Minutolo

  DOI：10.1021/acs.jafc.7b01668

  日期：2017.7.19

  Inhibition of lactate dehydrogenase (LDH) represents an innovative approach to tackle cancer because this peculiar glycolytic metabolism is characteristic of most invasive tumor cells. An investigation into the biological properties of saffron extracts led to the discover of their LDH-inhibition properties. In particular, the most important saffron components, crocetin, was found to inhibit LDH (IC50

  乳酸脱氢酶（LDH）的抑制代表了一种解决癌症的创新方法，因为这种独特的糖酵解代谢是大多数侵袭性肿瘤细胞的特征。对藏红花提取物生物学特性的研究导致发现了它们对LDH的抑制特性。特别是，发现最重要的藏红花成分藏红花素抑制LDH（IC 50 = 54.9±4.7μM）。该类胡萝卜素是通过化学合成独立产生的，其LDH抑制特性通过其对两种糖酵解癌细胞系（A549和HeLa，IC 50分别为114.0±8.0和113.0±11.1μM）。本文描述的结果表明，藏红花可能是预防癌症的有益饮食成分，可能有助于批准的癌症疗法的功效。