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Crocetin

$250

  • Brand : BIOFRON

  • Catalogue Number : BF-C4003

  • Specification : 98%(HPLC)

  • CAS number : 27876-94-4

  • Formula : C20H24O4

  • Molecular Weight : 328.4

  • PUBCHEM ID : 5281232

  • Volume : 25mg

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Catalogue Number

BF-C4003

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

328.4

Appearance

Red cryst.

Botanical Source

Crocus sativus,Gardenia jasminoides,Cryptomeria japonica

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=CC=CC=C(C)C=CC=C(C)C(=O)O)C=CC=C(C)C(=O)O

Synonyms

8,8'-Diapo-y,y-carotenedioic Acid/transcrocetin/2,4,6,8,10,12,14-Hexadecaheptaenedioic acid, 2,6,11,15-tetramethyl-, (2E,4E,6E,8E,10E,12E,14E)-/trans-Crocetin/carotenoid dicarboxylic acid/(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-Tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioic acid/8,8'-Diapocarotene-8,8'-dioic acid/all-trans-8,8'-diapocarotene-8,8'-dioic acid/Crocetin/Natural yellow 6/(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-Tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid/8,8'-Diapo-8,8'-carotenedioic acid/8,8'-Diapocarotenedioic acid

IUPAC Name

(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid

Applications

Transcrocetin (trans-Crocetin), extracted from saffron (Crocus sativus L.), acts as an NMDA receptor antagonist with high affinity.

Density

1.1±0.1 g/cm3

Solubility

Methanol; DMF; Pyridine; Weak base water

Flash Point

321.7±19.1 °C

Boiling Point

585.1±23.0 °C at 760 mmHg

Melting Point

285°

InChl

InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+

InChl Key

PANKHBYNKQNAHN-MQQNZMFNSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:27876-94-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29253763

Abstract

Crocetin is a natural product possessing extraordinary therapeutic effects for various diseases. However, its extremely low solubility limits its application greatly. Conjugation of organic compounds containing heteroatoms such as N to poor soluble molecules can help the synthesized derivative to form stable hydrogen bonds by lowering the salvation energy, which will improve the solubility of the synthesized compounds. Herein, crocetin was modified by conjugating with piperidyl, diethylin and benzylamine to improve their solubility and bioactivities. In the present study, the conjugation of crocetin with piperidyl, diethylin and benzylamine and their influence on the solubility and the pharmacological effects of crocetin were investigated. With the described strategy, crocetin derivatives were synthesized and their structures were elucidated by 1H NMR, 13C NMR and UPLC-MS spectroscopic analysis. The solubility of crocetin and its derivatives were identified. Upon that, the pharmacological effects of the crocetin derivatives on the tumor and inflammation treatment were investigated. It was shown that, in contrast to crocetin, of which, the solubility and pharmacological effects were low and limited, the synthesized compounds have significantly higher solubility and possess broad spectrum of anticancer effects in multiple tumor cell lines, including B16F10, MCF-7, A549 and SKOV3, as well as enhanced anti-inflammation efficacy in macrophage (RAW264.7) without causing cells damage. Conjugation of piperidyl, diethylin and benzylamine with the crocetin was demonstrated to be a highly efficient strategy to improve the solubility of crocetin. The synthesized crocetin derivatives were shown the promising therapeutics for the tumor and inflammation treatment with high safety.

KEYWORDS

Anti-inflammation; Crocetin derivatives; Solubility; Tumor inhibition.

Title

Synthesis, Characterization and Inhibitory Effects of Crocetin Derivative Compounds in Cancer and Inflammation

Author

Yang Chu 1 , Jin Gao 2 , Jie Niu 1 , Yan-Fen Huang 1 , Ming Chen 3 , Mao-Ze Wang 1 , Qiang Shang 4 , Wen-Qi Lu 4 , Li-Hua Peng 5 , Zhi-Hong Jiang 6

Publish date

2018 Feb

PMID

30477864

Abstract

Objectives: The aim of the present study was to investigate the effect of crocetin on sleep architecture and subjective sleep parameters in healthy adult participants with mild sleep complaints.
Design: A randomized, double-blind, placebo-controlled, crossover study with two intervention periods of 14 days each, separated by a 14-day wash-out period.
Interventions: Thirty participants were randomly assigned to one of two sequence groups. Each group was given crocetin at 7.5 mg/day, or placebo. We measured objective sleep parameters using single-channel electroencephalography and assessed subjective sleep parameters using the Oguri-Shirakawa-Azumi Sleep Inventory, Middle-age and Aged version (OSA-MA).
Main outcome measures: Differences between crocetin and placebo in an objective sleep parameter (delta power), and OSA-MA scores.
Results: Delta power was significantly increased with crocetin compared with placebo. There were no significant differences in the other sleep parameters, including sleep latency, sleep efficiency, total sleep time, and wake after sleep onset. Subjective scores for sleepiness on rising and feeling refreshed were significantly improved with crocetin compared with placebo.
Conclusions: The findings of the present study suggest that crocetin supplementation contributes to sleep maintenance, leading to improved subjective sleep quality.

KEYWORDS

Anti-inflammation; Crocetin derivatives; Solubility; Tumor inhibition.

Title

Effect of Crocetin on Quality of Sleep: A Randomized, Double-Blind, Placebo-Controlled, Crossover Study

Author

Naofumi Umigai 1 , Ryuji Takeda 2 , Atsuko Mori 3

Publish date

2018 Dec

PMID

28407293

Abstract

Natural products have gained a wide popularity as chemopreventive and anti-cancer agents owing to their multi-mechanistic mode of action, availability and synergism with several conventional chemotherapeutic agents. Crocetin is a carotenoid compound isolated from the stigma of Crocus sativus L. (saffron). Crocetin has shown promising effects as an anti-tumor agent in animal models and cell culture systems. Crocetin retards the growth of cancer cells via inhibiting nucleic acid synthesis, enhancing anti-oxidative system, and inducing apoptosis and differentiation pathways. The present review outlines natural sources of crocetin, and its pharmacokinetic and pharmacological properties relevant to the prevention and treatment of cancer. Also, we discuss molecular targets underlying the putative anti-tumor effects of crocetin.

KEYWORDS

Crocus sativus; cancer; crocetin; saffron.

Title

Anti-tumor Effects of Crocetin and Related Molecular Targets

Author

Maliheh Moradzadeh 1 , Hamid Reza Sadeghnia 1 2 , Alijan Tabarraei 3 , Amirhossein Sahebkar 4 Affiliations Expand

Publish date

2018 Mar