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Cas Database

27876-94-4

27876-94-4

Identification

  • Product Name:Crocetin

  • CAS Number: 27876-94-4

  • EINECS:248-708-0

  • Molecular Weight:328.408

  • Molecular Formula: C20H24O4

  • HS Code:29171900

  • Mol File:27876-94-4.mol

Synonyms:2,4,6,8,10,12,14-Hexadecaheptaenedioicacid, 2,6,11,15-tetramethyl-, (all-E)- (8CI);Crocetin (6CI);Crocetin(stable);NSC 407300;Stable crocetin;trans-Crocetin;2,4,6,8,10,12,14-Hexadecaheptaenedioicacid, 2,6,11,15-tetramethyl-, (2E,4E,6E,8E,10E,12E,14E)-;8,8'-Diapo-y,y-carotenedioic acid;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult 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.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. 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 Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. 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. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:Usbiological
  • Product Description:Crocetin
  • Packaging:10mg
  • Price:$ 490
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Crocetin
  • Packaging:5mg
  • Price:$ 95
  • Delivery:In stock
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Crocetin
  • Packaging:50 mg
  • Price:$ 610
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Transcrocetin >98%
  • Packaging:100 mg
  • Price:$ 550
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Transcrocetin >98%
  • Packaging:1 g
  • Price:$ 2200
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Transcrocetin >98%
  • Packaging:250 mg
  • Price:$ 1100
  • Delivery:In stock
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  • Manufacture/Brand:CSNpharm
  • Product Description:Crocetin
  • Packaging:50mg
  • Price:$ 569
  • Delivery:In stock
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  • Manufacture/Brand:CSNpharm
  • Product Description:Crocetin
  • Packaging:1mg
  • Price:$ 35
  • Delivery:In stock
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  • Manufacture/Brand:CSNpharm
  • Product Description:Crocetin
  • Packaging:10mg
  • Price:$ 124
  • Delivery:In stock
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  • Manufacture/Brand:CSNpharm
  • Product Description:Crocetin
  • Packaging:25mg
  • Price:$ 299
  • Delivery:In stock
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Relevant articles and documentsAll total 9 Articles be found

Trans-crocin 4 is not hydrolyzed to crocetin following i.p. administration in mice, while it shows penetration through the blood brain barrier

Karkoula, Evangelia,Lemonakis, Nikolaos,Kokras, Nikolaos,Dalla, Christina,Gikas, Evagelos,Skaltsounis, Alexios-Leandros,Tsarbopoulos, Anthony

, p. 62 - 72 (2018)

A novel, fit-for-purpose, highly sensitive, analytical UPLC-PDA methodology was developed and fully validated, according to ICH, FDA and EMA guidelines, for the rapid and accurate quantification of trans-crocin 4 (TC4) and crocetin (CRC) in mice plasma and brain after i.p. administration. A PDA based methodology shows a wider applicability as it is cost effective and can be easily and seamlessly adopted by the pharma industry. The separation of the analytes was performed on a C18 Hypersil Gold column with 2.5 min run time, employing the internal standard (ISTD) methodology. The two methods were successfully applied for the determination of CRC and TC4 in mouse plasma and brain after i.p. administration of TC4 (50 mg/kg) in a time range of 0–240 min. Due to the selection of i.p. administration route, the first-pass metabolism and/or gastric hydrolysis were bypassed, a fact that enhanced the bioavailability of TC4. Furthermore, TC4 was found to be capable of crossing the Blood Brain Barrier (BBB) and build up levels in the mouse brain, regardless of its highly hydrophilic character. CRC was not detected in any plasma or brain sample, although it has been reported that TC4 quickly hydrolyzes to CRC after p.o. administration. Therefore i.p. administration could be used in the case of TC4 for the accurate determination of its biological role. Overall, the developed methodology offers important information about the bioavailability of TC4 in mouse plasma and for the first time, demonstrates the ability of TC4 to penetrate the BBB and localize inside the brain.

Effects of intestinal microbiota on pharmacokinetics of crocin and crocetin in male sprague-dawley rats

Shakya, Rajina,Nepal, Mahesh R.,Kang, Mi Jeong,Jeong, Tae Cheon

, p. 1 - 10 (2020)

In addition to the hepatic metabolism, the role of intestinal microbiota in drug metabolism has been considered important in the biotransformation of xenobiotics. Crocin and its aglycone, crocetin, isolated from many plants, including the dried stigma of Crocus sativus and the fruit of Gardenia jasminoides, have been used in treatment of inflammation, cancer, and metabolic disorders. In this study, the effect of intestinal microbiota on the pharmacokinetics of crocin was studied following single oral treatment with 600 mg/kg crocin to male rats pre-treated with a mixture of antibiotics, such as cefadroxil, oxytetracycline, and erythromycin, for three consecutive days. Following crocin treatment, blood, urine, and feces were collected at various time points for evaluating pharmacokinetic characteristics of crocin and crocetin by using LC-MS. Results showed that intestinal absorption of crocin was relatively marginal when compared with that of crocetin, and that crocin metabolism to crocetin by intestinal microbiota would be a critical step for absorption. The present results clearly suggested that the in vivo pharmacological effects of crocin might be considered as the effects by its aglycone, crocetin, mainly, and that the metabolism of glycosidic natural products by intestinal microbiota should be considered to understand their pharmacodynamic actions.

Crocetin diester compound as well as preparation method and application thereof

-

Paragraph 0012; 0024-0026, (2021/03/30)

The invention belongs to the technical field of pesticides, and provides a crocetin diester compound as well as preparation and application thereof in plant protection. It is found for the first timethat natural products crocin-1 and crocin-2 show higher anti-plant virus activity level than commercial variety virazole, can be used as a novel botanical pesticide or used as a lead compound for development, and used as the lead to design and synthesize the crocetin diester compound. An anti-plant virus activity test shows that all the compounds show activity on tobacco mosaic viruses, and particularly, the activity level of the crocetin di (4-fluorophenyl ethyl) ester is higher than that of a lead compound.

Preparation and Anti-Tobacco Mosaic Virus Activities of Crocetin Diesters

Chen, Guihua,Deng, Zhaoyang,Li, Ling,Liu, Yuxiu,Wang, Qingmin,Xu, Changjiang,You, Shengyong,Zou, Jiyong

, p. 13637 - 13643 (2021/11/18)

The development of antiviral agents with an original structure and noticeable effect is always in great need. Natural products are important lead compounds in the development of new pesticides. Crocin-1 and crocin-2 were effectively isolated from Gardeniae fructus and found to have higher anti-tobacco mosaic virus (TMV) activity levels than ribavirin. A series of the crocetin diester derivatives were synthesized with separated crocetin-1 as material and evaluated for their anti-TMV activities. They could be dissolved in common organic solvents as dichloromethane, ethyl acetate, tetrahydrofuran, and methanol. Compounds 5, 9, 13, 14, and 15 displayed higher activities in vivo than ribavirin. Compound 14 with significantly higher antiviral activities than lead compounds (crocin-1 and crocin-2) emerged as a new antiviral candidate.

The crocetin single-glucuronic acid synthesis method (by machine translation)

-

Paragraph 0035; 0036, (2018/12/14)

The invention relates to a metabolism in vivo product synthesis method. The method comprises the following steps: from traditional Chinese medicine fructus Gardeniae extracting the separated crocin, and crocin hydrolyzed into crocetin, to west pertains as substrate of synthetic west pertains to the fluoro, with fluoro and for D - glucuronic acid reaction to produce the target compound - crocetin single-glucuronic acid. The synthesis method principle is simple, easy to operate, low requirements on equipment, which can be widely applied. (by machine translation)

Process route upstream and downstream products

Process route

Conditions
Conditions Yield
crocin; With sodium hydroxide; water; at 50 ℃; for 3.5h;
With phosphoric acid; In water; at 20 ℃; for 3h;
With potassium hydroxide; at 65 ℃; for 2h;
With potassium hydroxide; at 100 - 105 ℃;
With water; sodium hydroxide; at 100 ℃; for 3h;
With water; sodium hydroxide; at 100 ℃; for 3h;
0.6 g
crocin-4
55750-86-2

crocin-4

crocetin
27876-94-4

crocetin

Conditions
Conditions Yield
With water; sodium hydroxide; at 60 ℃; for 4h;
(2E,4E,6E,10E,12E,14E)-2,6,11,15-Tetramethyl-hexadeca-2,4,6,10,12,14-hexaen-8-ynedioic acid ethyl ester 2-formyl-2-hydroxy-1,3,3-trimethyl-cyclohexyl ester
35482-80-5

(2E,4E,6E,10E,12E,14E)-2,6,11,15-Tetramethyl-hexadeca-2,4,6,10,12,14-hexaen-8-ynedioic acid ethyl ester 2-formyl-2-hydroxy-1,3,3-trimethyl-cyclohexyl ester

crocetin
27876-94-4

crocetin

Conditions
Conditions Yield
With quinoline; hydrogen; Lindlar's catalyst;
<3-(Methoxycarbonyl)-2-butenyl>triphenylphosphoniumbromid
121666-37-3

<3-(Methoxycarbonyl)-2-butenyl>triphenylphosphoniumbromid

crocetin
27876-94-4

crocetin

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: sodium hydroxide / dichloromethane; water / 20 °C
2: toluene / 6 h / 130 °C / Reflux
3: sodium hydroxide / water; methanol / Reflux
4: phosphoric acid
With phosphoric acid; sodium hydroxide; In methanol; dichloromethane; water; toluene;
2-methyl-4-(triphenyl-λ<sup>5</sup>-phosphoranylidene)but-2-enoic acid methyl ester
129144-90-7

2-methyl-4-(triphenyl-λ5-phosphoranylidene)but-2-enoic acid methyl ester

crocetin
27876-94-4

crocetin

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: toluene / 6 h / 130 °C / Reflux
2: sodium hydroxide / water; methanol / Reflux
3: phosphoric acid
With phosphoric acid; sodium hydroxide; In methanol; water; toluene;
Ethyl (2E,4E)-2-methyl-6-oxohexa-2,4-dienoate
130121-15-2

Ethyl (2E,4E)-2-methyl-6-oxohexa-2,4-dienoate

crocetin
27876-94-4

crocetin

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: dichloromethane / 2 h / 20 °C
2: diisobutylaluminium hydride / hexane / 3 h / -78 - -20 °C / Inert atmosphere
3: manganese(IV) oxide / acetone / 0 - 20 °C
4: toluene / 6 h / 130 °C / Reflux
5: sodium hydroxide / water; methanol / Reflux
6: phosphoric acid
With manganese(IV) oxide; phosphoric acid; diisobutylaluminium hydride; sodium hydroxide; In methanol; hexane; dichloromethane; water; acetone; toluene;
diethyl 2,7-dimethyl-2(E),4(E),6(E)-octatriene-1,8-dioate
64768-01-0

diethyl 2,7-dimethyl-2(E),4(E),6(E)-octatriene-1,8-dioate

crocetin
27876-94-4

crocetin

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: diisobutylaluminium hydride / hexane / 3 h / -78 - -20 °C / Inert atmosphere
2: manganese(IV) oxide / acetone / 0 - 20 °C
3: toluene / 6 h / 130 °C / Reflux
4: sodium hydroxide / water; methanol / Reflux
5: phosphoric acid
With manganese(IV) oxide; phosphoric acid; diisobutylaluminium hydride; sodium hydroxide; In methanol; hexane; water; acetone; toluene;
(2E,4E,6E)-2,6-dimethylocta-2,4,6-triene-1,8-diol
113951-62-5

(2E,4E,6E)-2,6-dimethylocta-2,4,6-triene-1,8-diol

crocetin
27876-94-4

crocetin

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: manganese(IV) oxide / acetone / 0 - 20 °C
2: toluene / 6 h / 130 °C / Reflux
3: sodium hydroxide / water; methanol / Reflux
4: phosphoric acid
With manganese(IV) oxide; phosphoric acid; sodium hydroxide; In methanol; water; acetone; toluene;
(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial
5056-17-7

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

crocetin
27876-94-4

crocetin

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: toluene / 6 h / 130 °C / Reflux
2: sodium hydroxide / water; methanol / Reflux
3: phosphoric acid
With phosphoric acid; sodium hydroxide; In methanol; water; toluene;
Tiglic acid
80-59-1

Tiglic acid

crocetin
27876-94-4

crocetin

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: sulfuric acid / 24 h / 90 °C / Sealed tube
2.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
2.2: 20 °C
3.1: sodium hydroxide / dichloromethane; water / 20 °C
4.1: toluene / 6 h / 130 °C / Reflux
5.1: sodium hydroxide / water; methanol / Reflux
6.1: phosphoric acid
With N-Bromosuccinimide; phosphoric acid; sulfuric acid; sodium hydroxide; dibenzoyl peroxide; In methanol; dichloromethane; chloroform; water; toluene;

Global suppliers and manufacturers

Global( 95) Suppliers
  • Company Name
  • Business Type
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  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Shaanxi BLOOM TECH Co.,Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-29-86470566
  • Emails:sales@bloomtechz.com
  • Main Products:79
  • Country:China (Mainland)
  • Shanghai Upbio Tech Co.,Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-21-52196435
  • Emails:upbiocn@hotmail.com
  • Main Products:88
  • Country:China (Mainland)
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