| Name: | bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate |
| CAS Number: | 42553-65-1 |  3D/inchi
|
| Other(deleted CASRN): | 11012-59-2 |
| ECHA EINECS - REACH Pre-Reg: | 255-881-6 |
| FDA UNII: | 877GWI46C2 |
| Nikkaji Web: | J16.015F |
| Beilstein Number: | 6473367 |
| MDL: | MFCD00017495 |
| XlogP3-AA: | -2.50 (est) |
| Molecular Weight: | 976.97488000 |
| Formula: | C44 H64 O24 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 1169.04 °C. @ 760.00 mm Hg (est)
|
| Flash Point: | 640.00 °F. TCC ( 337.80 °C. ) (est)
|
| logP (o/w): | -4.742 (est) |
| Soluble in: |
| | water, 3688 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
| Alfa Biotechnology |
| For experimental / research use only. |
| Crocin I 98%
|
| BOC Sciences |
| For experimental / research use only. |
| CroCin
|
| Changsha Organic Herb |
| Saffron Extract Power Crocus sativus L.
|
| Coompo |
| For experimental / research use only. |
| Crocin from Plants ≥98%
Odor: characteristic Use: Crocus sativus L., commonly known as saffron, is used in folk medicine for various purposes. Modern pharmacological studies have demonstrated that saffron extracts have antitumour effects, radical scavenger properties or hypolipaemic effects. 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. Saffron extract improved ethanol-induced impairments of learning behaviours in mice, 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 saffron extract is attributed to crocin (crocetin di-gentiobiose ester), but not crocetin. Saffron extract or its active constituents, crocetin and crocin, could be useful as a treatment for neurodegenerative disorders accompanying memory impairment.
Crocin has been shown to be a potent antioxidant. It 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.
Crocin inhibitors of pancreatic lipase with an IC50 value of 2.6 mg/ml (triolein as a substrate). Crocin significantly inhibited the increase of serum TG level in corn oil feeding-induced triglyceridemic mice, as well as that of serum triglyceride and total and LDL cholesterol levels in Triton WR-1339-induced hyperlipidemic mice. These compounds also showed hypolipidemic activity in hyperlipidemic mice 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. |
| ExtraSynthese |
| For experimental / research use only. |
| Crocin
|
| Sigma-Aldrich: Sigma |
| For experimental / research use only. |
| Crocin for microscopy
|
Safety Information:
| Preferred SDS: View |
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
|
| Dermal Toxicity: |
subcutaneous-mouse LDLo 10000 mg/kg
PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Japanese Journal of Pharmacology. Vol. 4, Pg. 69, 1954.
|
| Inhalation Toxicity: |
|
Not determined
|
Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for crocetin digentiobiose ester usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for crocetin digentiobiose ester flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
| EPI System: View |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5281233 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate |
| Chemidplus:0042553651 |
| RTECS:HL7380000 for cas# 42553-65-1 |
References:
| | bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 5281233 |
| Pubchem (sid): | 135079256 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| all-trans- | crocetin di-β-D-gentiobiosyl ester | | | crocin | | a- | crocin | | 8,8'- | diapo-psi,psi-carotenedioic acid, bis(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester | | 8,8'- | diapo-y,y-carotenedioic acid bis(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl) ester | | | gardenia yellow | | | saffron (natural color) | | bis[(2S,3R,4S,5S,6R)-3,4,5- | trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate |
Articles:
| PubMed:Identifying a Carotenoid Cleavage Dioxygenase 4a Gene and Its Efficient Agrobacterium-Mediated Genetic Transformation in Bixa orellana L. |
| PubMed:Crocin loaded nano-emulsions: Factors affecting emulsion properties in spontaneous emulsification. |
| PubMed:Evidence of neuroprotective effects of saffron and crocin in a Drosophila model of parkinsonism. |
| PubMed:Reversal effects of crocin on amyloid β-induced memory deficit: Modification of autophagy or apoptosis markers. |
| PubMed:Metabolomics-Based Screening of Biofilm-Inhibitory Compounds against Pseudomonas aeruginosa from Burdock Leaf. |
| PubMed:Antioxidant effect of crocin on bovine sperm quality and in vitro fertilization. |
| PubMed:Protective effect of Crocin against zearalenone-induced oxidative stress in liver and kidney of Balb/c mice. |
| PubMed:Zearalenone-induced changes in biochemical parameters, oxidative stress and apoptosis in cardiac tissue: Protective role of crocin. |
| PubMed:Inhibitory effect of apocarotenoids on the activity of tyrosinase: Multi-spectroscopic and docking studies. |
| PubMed:Crocin and Quercetin protect HCT116 and HEK293 cells from Zearalenone-induced apoptosis by reducing endoplasmic reticulum stress. |
| PubMed:Optimization of ultrasound-assisted extraction of gardenia fruit oil with bioactive components and their identification and quantification by HPLC-DAD/ESI-MS(2). |
| PubMed:Improvement of crocin stability by biodegradeble nanoparticles of chitosan-alginate. |
| PubMed:Saffron as an antidote or a protective agent against natural or chemical toxicities. |
| PubMed:Efficacy and Safety of Saffron Supplementation: Current Clinical Findings. |
| PubMed:Anti-asthma potential of crocin and its effect on MAPK signaling pathway in a murine model of allergic airway disease. |
| PubMed:Measuring antioxidant and prooxidant capacity using the Crocin Bleaching Assay (CBA). |
| PubMed:Safranal, a Crocus sativus L constituent suppresses the growth of K-562 cells of chronic myelogenous leukemia. In silico and in vitro study. |
| PubMed:Crocin bleaching antioxidant assay revisited: application to microplate to analyse antioxidant and pro-oxidant activities. |
| PubMed:Antitumor effects of saffron-derived carotenoids in prostate cancer cell models. |
| PubMed:Evaluation of crocin and curcumin affinity on mushroom tyrosinase using surface plasmon resonance. |
| PubMed:Effect of split foliar fertilisation on the quality and quantity of active constituents in saffron (Crocus sativus L.). |
| PubMed:Bioactivity assessment and toxicity of crocin: a comprehensive review. |
| PubMed:Preparative separation of crocins and geniposide simultaneously from gardenia fruits using macroporous resin and reversed-phase chromatography. |
| PubMed:Evaluation of teratogenic effects of crocin and safranal, active ingredients of saffron, in mice. |
| PubMed:Characterisation of secondary metabolites in saffron from central Italy (Cascia, Umbria). |
| PubMed:Changes in total and individual crocetin esters upon in vitro gastrointestinal digestion of saffron aqueous extracts. |
| PubMed:Crocin, a dietary colorant, mitigates cyclophosphamide-induced organ toxicity by modulating antioxidant status and inflammatory cytokines. |
| PubMed:Antihyperglycemic and antioxidant activity of crocin in streptozotocin-induced diabetic rats. |
| PubMed:Dietary Crocin Inhibits Colitis and Colitis-Associated Colorectal Carcinogenesis in Male ICR Mice. |
| PubMed:Saffron: A Natural Potent Antioxidant as a Promising Anti-Obesity Drug. |
| PubMed:Crocin, a dietary additive protects platelets from oxidative stress-induced apoptosis and inhibits platelet aggregation. |
| PubMed:UGT75L6 and UGT94E5 mediate sequential glucosylation of crocetin to crocin in Gardenia jasminoides. |
| PubMed:An on-line high performance liquid chromatography-crocin bleaching assay for detection of antioxidants. |
| PubMed:Enrichment and purification of gardenia yellow from Gardenia jasminoides var. radicans Makino by column chromatography technique. |
| PubMed:Crocin promotes non-rapid eye movement sleep in mice. |
| PubMed:Effect of sucrose in different commonly used pediatric medicines upon plaque pH in human subjects. |
| PubMed:[Preparation of crocin from gardenia yellow pigment by slow rotary countercurrent chromatography]. |
| PubMed:Saffron (Crocus sativus) aqueous extract and its constituent crocin reduces stress-induced anorexia in mice. |
| PubMed:Consideration of fluorescence properties for the direct determination of erythrosine in saffron in the presence of other synthetic dyes. |
| PubMed:A new method research for determination of natural pigment crocin yellow in foods by solid-phase extraction ultrahigh pressure liquid chromatography. |
| PubMed:Sub-acute effects of diazinon on biochemical indices and specific biomarkers in rats: protective effects of crocin and safranal. |
| PubMed:Crocin attenuates cisplatin-induced renal oxidative stress in rats. |
| PubMed:Quantification of crocetin esters in saffron (Crocus sativus L.) using Raman spectroscopy and chemometrics. |
| PubMed:Preventive effect of crocin in inflamed animals and in LPS-challenged RAW 264.7 cells. |
| PubMed:Further examination of antiradical properties of Crocus sativus stigmas extract rich in crocins. |
| PubMed:Structure-dependent photodegradation of carotenoids accelerated by dimethyl tetrasulfide under UVA irradiation. |
| PubMed:Spectroscopic, stability and radical-scavenging properties of a novel pigment from gardenia. |
| PubMed:Biotransformation of ginsenoside Rb1, crocin, amygdalin, geniposide, puerarin, ginsenoside Re, hesperidin, poncirin, glycyrrhizin, and baicalin by human fecal microflora and its relation to cytotoxicity against tumor cells. |
| PubMed:Composition of phenolic compounds and antioxidant activity of commercial aqueous smoke flavorings. |
| PubMed:Mechanism of deactivation of triplet-excited riboflavin by ascorbate, carotenoids, and tocopherols in homogeneous and heterogeneous aqueous food model systems. |
| PubMed:Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo. |
| PubMed:Crocin bleaching assay (CBA) in structure-radical scavenging activity studies of selected phenolic compounds. |
| PubMed:Inhibitory activity on amyloid-beta aggregation and antioxidant properties of Crocus sativus stigmas extract and its crocin constituents. |
| PubMed:Crocin bleaching assay step by step: observations and suggestions for an alternative validated protocol. |
| PubMed:Trametes versicolor: a possible tool for aflatoxin control. |
| PubMed:Radical scavenging activity of Crocus sativus L. extract and its bioactive constituents. |
| PubMed:Orally administered crocetin and crocins are absorbed into blood plasma as crocetin and its glucuronide conjugates in mice. |
| PubMed:Effect of drying temperature and air flow on the production and retention of secondary metabolites in saffron. |
| PubMed:Screening method for the detection of artificial colours in saffron using derivative UV-Vis spectrometry after precipitation of crocetin. |
| PubMed:Influence of different drying and aging conditions on saffron constituents. |
| PubMed:The chemistry behind antioxidant capacity assays. |
| PubMed:Use of in vitro assays to assess the potential antigenotoxic and cytotoxic effects of saffron (Crocus sativus L.). |
| PubMed:Role of component herbs in antioxidant activity of shengmai san--a traditional Chinese medicine formula preventing cerebral oxidative damage in rat. |
| PubMed:Antioxidant Activity of Anthocyanin Extract from Purple Black Rice. |
| PubMed:Coffee drinking influences plasma antioxidant capacity in humans. |
| PubMed:A new automated method for the determination of the Total Antioxidant Capacity (TAC) of human plasma, based on the crocin bleaching assay. |
| PubMed:Genotoxicity of gardenia yellow and its components. |
| PubMed:Assessment of pro-oxidant activity of foods by kinetic analysis of crocin bleaching. |
| PubMed:Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study. |
| PubMed:Comparative study of ovatifolin antioxidant and growth inhibition activities. |
| PubMed:Progress of the Maillard reaction and antioxidant action of Maillard reaction products in preheated model systems during storage. |
| PubMed:Antioxidant properties of crocin from Gardenia jasminoides Ellis and study of the reactions of crocin with linoleic acid and crocin with oxygen. |
| PubMed:Modulation of programmed cell death by medicinal plants. |
| PubMed:Kinetic analysis of antioxidant capacity of wine. |
| PubMed:Kinetics of reduction of hypervalent iron in myoglobin by crocin in aqueous solution. |
| PubMed:In vitro formation of crocetin glucosyl esters by Crocus sativus callus extract. |
| PubMed:Clonal multiplication of Gardenia jasminoides Ellis through axillary bud culture. |
| PubMed:A study on the toxicity of natural food dyes--toxicity and enzyme inhibition in Paramecium caudatum. |
| PubMed:Co-oxydation of a carotenoid by the enzyme lipoxygenase: influence on the formation of linoleic acid hydroperoxides. |
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