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CROCETIN

CAS NUMBER: 27876-94-4

EC NUMBER: 248-708-0

MOLECULAR FORMULA: C20H24O4

MOLECULAR WEIGHT: 328,402 g/mol

 

Crocetin is a natural apocarotenoid dicarboxylic acid that is found in the crocus flower together with its glycoside, crocin, and Gardenia jasminoides fruits.
Crocetin forms brick red crystals with a melting point of 285°C.

The chemical structure of crocetin forms the central core of crocin, the compound responsible for the color of saffron.
Crocetin transcrocetinate sodium (INN, also known as trans sodium crocetinate or TSC) is an experimental drug that increases the movement of oxygen from red blood cells into hypoxic (oxygen-starved) tissues.

Crocetin belongs to a group of substances known as bipolar trans carotenoid salts, which constitute a subclass of oxygen diffusion-enhancing compounds.
Crocetin was one of the first such compounds discovered.

Crocetin can be prepared by reacting saffron with sodium hydroxide and extracting the salt of the trans crocetin isomer from the solution.
Crocetin have been investigated the effects of transcrocetinate sodium.

They discovered that Crocetin could reverse the potentially fatal decrease in blood pressure produced by the loss of large volumes of blood in severe hemorrhage, and thereby improve survival.
Early investigations of Crocetin suggested that it had potential applications in battlefield medicine, specifically in treatment of the many combat casualties with hemorrhagic shock.

Crocetin might prove beneficial in the treatment of a variety of conditions associated with hypoxia and ischemia (a lack of oxygen reaching the tissues, usually due to a disruption in the circulatory system), including cancer, myocardial infarction (heart attack), and stroke.
Crocetin has shown promise of effectiveness in restoring tissue oxygen levels and improving the ability to walk in a clinical trial of patients with peripheral artery disease in which reduced delivery of oxygen-rich blood to tissues can cause severe leg pain and impair mobility. 

Crocetin has also been under investigation in a clinical trial sponsored by drug developer Diffusion Pharmaceuticals for potential use as a radiosensitizer, increasing the susceptibility of hypoxic cancer cells to radiation therapy, in patients with a form of brain known as glioblastoma.
Crocetin is currently under investigation for its possible use in enhancing the oxygenation status of COVID-19 patients at risk for developing multiple organ failure due to severe respiratory distress.

Similar to other oxygen diffusion-enhancing compounds, transcrocetinate sodium appears to improve oxygenation in hypoxic tissues by exerting hydrophobic effects on water molecules in blood plasma and thereby increasing the hydrogen bonding between the water molecules.
This in turn causes the overall organization of water molecules in plasma to become more structured, which facilitates the diffusion of oxygen through plasma and promotes the movement of oxygen into tissues.

Crocetin has been found to act as an NMDA receptor antagonist with high affinity, and has been implicated in the psychoactivity of saffron.
Crocetin is a 20-carbon dicarboxylic acid which is a diterpenoid and natural carotenoid. 

Found in the crocus flower, it has been administered as an anti-fatigue dietary supplement. 
Crocetin has a role as a nutraceutical, a metabolite and an antioxidant. 

Crocetin is a carotenoic acid, a diterpenoid and a polyunsaturated dicarboxylic acid. 
Crocetin is a conjugate acid of a crocetin(2-).

Crocetin is a polyene dicarboxylic acid with two lipophobic free carboxylic groups and lipophilic polyene structure, which are responsible for the poor solubility in various solvents. 
Crocetin has a great prospective in the treatment of many life-threatening diseases. 

The poor solubility of the crocetin greatly restricts its dose-dependent effects and bioavailability.
To enhance the solubility of crocetin, many scientific groups had either used various types of solubilizer or incorporated the compound in other drug-delivery vehicles. 

The use of solubilizers and other compounds to enhance the solubility of crocetin did not reveal the exact results of crocetin and the biological safety of the drug formulation. 
As a result, derivatives of the crocetin were made to enhance Crocetins solubility and are useful for its efficacy and application. 

Till date, fewer studies have been reported on the influence of chemical modification on the solubility and biological effect of crocetin. 
Crocetin has been described in literature that the replacement of the acid group by amide group increases lipophilicity and that the permeability of the compounds could be enhanced by incorporating alkyl chain to amino moiety. 

However, large compounds having an amide group play an important role in the synthesis of many biological as well as pharmaceutical products.
Crocetin has a protective effect against LPS-induced acute lung injury. 

Crocetin significantly decreased LPS-induced elevation of macrophage chemoattractant protein-1 (MCP-1) in the lung tissue. 
Also, crocetin decreased phospho-IκB expression and NF-κB activity in the lung tissue which had been induced by LPS

Crocetin is a natural carotenoid dicarboxylic acid that is found in the crocus flower. 
Crocetin forms brick red crystals with a melting point of 285 °C.

Crocetin is a natural apocarotenoid dicarboxylic acid that is found in the crocus flower together with its glycoside, crocin, and Gardenia jasminoides fruits. 
Crocetin forms brick red crystals with a melting point of 285°C. 

The chemical structure of crocetin forms the central core of crocin, the compound responsible for the color of saffron.
Crocetin is an aglycon of carotenoid extracted by saffron stigmas and known to have a potent anti-oxidative effect. 

Crocetin is reported to have neurotoxicity partly via oxidative stress. 
In this study, we investigated the effect of crocetin on hippocampal HT22 cell death induced by Aβ1-42. 

Furthermore, to clarify the mechanism underlying the protective effects of crocetin against Aβ1-42- induced cell death, we measured reactive oxygen species (ROS) production by CM-H2DCFDA kit assay. Crocetin at 1 -10 μM protected HT22 cells against Aβ1-42-induced neuronal cell death and decreased ROS production increased by Aβ1-42. These results that crocetin has the potent neuroprotective effect against Aβ1-42-induced cytotoxicity in hippocampal cells by attenuating oxidative stress, suggest that crocetin may provide a useful therapeutic strategy against Aβ-related disorders.
A bright yellow natural dyestuff. 

Crocetin is the primary colorant in Saffron, crocus, Wongsky, unki, gunari, and flowers of Nyctanthes arbor-tristis. 
Crocetin is a Substantive dye that produces a strong yellow color on Alum mordanted and unmordanted Wool. 

Copper mordanting produces a greenish yellow shade.
Soluble dilute alkali solutions and pyridine. 

Slightly soluble in water, organic solvents.
Forms a blue solution in concentrated sulfuric acid.

Forms dark red crystals from acetic anhydride extract.
Among the constituents of saffron extract, crocetin is mainly responsible for these pharmacological activities. 

In addition, recent behavioural and electrophysiological studies have demonstrated that saffron extract affects learning and memory in experimental animals. 
Crocetin extract improved ethanol-induced impairments of learning behaviours and prevented ethanol-induced inhibition of hippocampal long-term potentiation, a form of activity-dependent synaptic plasticity that may underly learning and memory. 

This effect of Crocetin is attributed to crocin, but not crocetin. 
Crocetins active constituents, crocetin and crocin, could be useful as a treatment for neurodegenerative disorders accompanying memory impairment. ,

Crocetin has been shown to be a potent antioxidant. 
Crocetin has also been shown to have an anticarcinogenic action. 

In rodents, crocin has been shown to have antidepressant properties and one study reports aphrodisiac properties. 
Crocetin inhibitors of pancreatic lipase with an IC50 value of 2.6 mg/ml (triolein as a substrate). 

Crocetin significantly inhibited the increase of serum TG level in corn oil feeding-induced triglyceridemic, as well as that of serum triglyceride and total and LDL cholesterol levels in Triton WR-1339-induced hyperlipidemic.
These compounds also showed hypolipidemic activity in hyperlipidemic induced by high cholesterol, high fat or high carbohydrate diets for 5 weeks. 

The results suggest that the hypolipidemic activity of GF and its component crocin may be due to the inhibition of pancreatic lipase and crocin can improve hyperlipidemia.
Crocetin is a natural apocarotenoid dicarboxylic acid that is found in the Crocus Sativus flower and Gardenia Jasminoides. 

Crocetin forms brick red crystals with a melting point of 285 °C.
The chemical structure of Crocetin forms the central core of Crocin, the compound responsible for the color of Saffron.

Crocetin has anti-convulsive properties. 
Crocetin is also believed to stimulate oxygen diffusivity during shock and reperfusion. 

Crocetin has anti-inflammatory properties, thus decreasing the risks of arthritis. 
Crocetin also has antioxidant properties, which could be responsible for inhibition of tumor formation.

Crocetin affects the growth cells by inhibiting nucleic acid synthesis, enhancing anti-oxidative system, inducing apoptosis and hindering growth factor signaling pathways.
Crocetin is a natural apocarotenoid dicarboxylic acid obtained from saffron, and saffron isa spice from the flower of the Saffron crocus and present in the dry stigmas of theplant Crocus sativus which can be used as a food colorant. 

Crocetin is reported to be anovel agent against hepatocellular skin, and colorectal.
Crocetin inhibits the nucleicacid synthesis, enhances antioxidant system, induces apoptosis, hinders growthfactor signaling pathways, and thus affects the growth of cells. 
Crocetin showseffects in the reduction of LPS-induced nitric oxide release; in the reduction ofproduced IL-1β, TNF-α, and intracellular ROS; in the activation of NF-κB; and inthe blockade of LPS.

 

USES:

Crocetin is derived from saffron, and is shown to have effects.

 

CHEMICAL PROPERTIES:

Red, rhomboid crystals.
Soluble in pyridine and dilute sodium hydroxide; slightly soluble in water and organic solvents. 
Combustible.

 

SYNONYM:

Transcrocetin
8,8'-Diapocarotenedioic acid
trans-Crocetin
Transcrocetinate
(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid
8,8'-Diapo-psi,psi-carotenedioic acid
8,8'-Diapocarotene-8,8'-dioic acid
UNII-20TC155L9C
CHEBI:3918
CHEMBL464792
LEAF-4L6715
20TC155L9C
27876-94-4 (free acid)
8,8'-diapo-8,8'-carotenedioic acid
alpha-Crocetin
.alpha.-Crocetin
CCRIS 7484
Transcrocetin [INN]
EINECS 248-708-0
NSC 407300
alpha Crocetin
Crocetin aglycon
NSC407300
NSC-407300
Transcrocetin [USAN]
trans-Crocetin - 98%
8,8'-Diapo-.psi.,.psi.-carotenedioic acid
Croceic Acid; Transcrocetin
8,8-Diapocarotenedioic acid
Saffron C.I. 75100
SCHEMBL20977
8,8''-diapocarotenedioic acid
LEAF-4L7520

 

 

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