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picrocrocin
1-cyclohexene-1-carboxaldehyde, 4-(beta-D-glucopyranosyloxy)-2,6,6-trimethyl-, (R)-

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Name:(4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde
CAS Number: 138-55-6Picture of molecule3D/inchi
FDA UNII: ON5B022511
Nikkaji Web:J5.635I
XlogP3-AA:-0.50 (est)
Molecular Weight:330.37762000
Formula:C16 H26 O7
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 520.40 °C. @ 760.00 mm Hg (est)
Flash Point: 369.00 °F. TCC ( 187.10 °C. ) (est)
logP (o/w): -0.240 (est)
Soluble in:
 water, 7707 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Picrocrocin 98%
BOC Sciences
For experimental / research use only.
1-Cyclohexene-1-carboxaldehyde,4-(b-D-glucopyranosyloxy)-2,6,6-trimethyl-,(4R)-
Santa Cruz Biotechnology
For experimental / research use only.
Picrocrocin
 
Safety Information:
 
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:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for picrocrocin usage levels up to:
 not for fragrance use.
 
Recommendation for picrocrocin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :130796
National Institute of Allergy and Infectious Diseases:Data
(4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde
Chemidplus:0000138556
 
References:
 (4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):130796
Pubchem (sid):135087365
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C17055
HMDB (The Human Metabolome Database):HMDB05796
FooDB:FDB014885
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 saffron flower
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 saffron oil
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 saffron stigma
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 saffron tissue culture
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Synonyms:
1-cyclohexene-1-carboxaldehyde, 4-(beta-D-glucopyranosyloxy)-2,6,6-trimethyl-, (R)-
(R)-4-(beta-D-glucopyranosyl oxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde
(R)-4-(beta-dextro-glucopyranosyl oxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde
 saffron-bitter
(4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde
 

Articles:

PubMed:Novel carotenoid cleavage dioxygenase catalyzes the first dedicated step in saffron crocin biosynthesis.
PubMed:Determination of saffron quality by high-performance liquid chromatography.
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:Relative expression of CsZCD gene and apocarotenoid biosynthesis during stigma development in Crocus sativus L.
PubMed:Characterisation of secondary metabolites in saffron from central Italy (Cascia, Umbria).
PubMed:Comparative reverse screening approach to identify potential anti-neoplastic targets of saffron functional components and binding mode.
PubMed:Revisiting extraction of bioactive apocarotenoids from Crocus sativus L. dry stigmas (saffron).
PubMed:Is there any interaction between telomeric DNA structures, G-quadruplex and I-motif, with saffron active metabolites?
PubMed:Avicenna's (Ibn Sina) the Canon of Medicine and saffron (Crocus sativus): a review.
PubMed:Quantification of main bioactive metabolites from saffron (Crocus sativus) stigmas by a micellar electrokinetic chromatographic (MEKC) method.
PubMed:Comparison of different tandem mass spectrometric techniques (ESI-IT, ESI- and IP-MALDI-QRTOF and vMALDI-TOF/RTOF) for the analysis of crocins and picrocrocin from the stigmas of Crocus sativus L.
PubMed:Picrocrocin kinetics in aqueous saffron spice extracts (Crocus sativus L.) upon thermal treatment.
PubMed:Extraction of crocin from saffron (Crocus sativus) using molecularly imprinted polymer solid-phase extraction.
PubMed:Crocus sativus L.: A comprehensive review.
PubMed:Crocins transport in Crocus sativus: the long road from a senescent stigma to a newborn corm.
PubMed:Effects of mild temperature conditions during dehydration procedures on saffron quality parameters.
PubMed:Picrocrocin content and quality categories in different (345) worldwide samples of saffron ( Crocus sativus L.).
PubMed:Metabolite and target transcript analyses during Crocus sativus stigma development.
PubMed:Parabens as agents for improving crocetin esters' shelf-life in aqueous saffron extracts.
PubMed:Interaction of safranal and picrocrocin with ctDNA and their preferential mechanisms of binding to GC- and AT-rich oligonucleotides.
PubMed:Bacillus subtilis FZB24 affects flower quantity and quality of saffron (Crocus sativus).
PubMed:Effect of centrifugal ultrafiltration on the composition of aqueous extracts of saffron spice (Crocus sativus L.).
PubMed:Quality and functionality of saffron: quality control, species assortment and affinity of extract and isolated saffron compounds to NMDA and sigma1 (sigma-1) receptors.
PubMed:Rapid determination of crocetin esters and picrocrocin from saffron spice (Crocus sativus L.) using UV-visible spectrophotometry for quality control.
PubMed:Determination of total safranal by in situ acid hydrolysis in supercritical fluid media: Application to the quality control of commercial saffron.
PubMed:A new approach to saffron aroma.
PubMed:Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo.
PubMed:Crocetin esters, picrocrocin and its related compounds present in Crocus sativus stigmas and Gardenia jasminoides fruits. Tentative identification of seven new compounds by LC-ESI-MS.
PubMed:Near-infrared spectroscopy in saffron quality control: determination of chemical composition and geographical origin.
PubMed:Influence of different drying and aging conditions on saffron constituents.
PubMed:Glucosylation of the saffron apocarotenoid crocetin by a glucosyltransferase isolated from Crocus sativus stigmas.
PubMed:[In vitro evaluation of the chemopreventive potential of saffron].
PubMed:Oxidative remodeling of chromoplast carotenoids: identification of the carotenoid dioxygenase CsCCD and CsZCD genes involved in Crocus secondary metabolite biogenesis.
PubMed:Membrane associated antitumor effects of crocine-, ginsenoside- and cannabinoid derivates.
PubMed:Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro.
PubMed:Determination of saffron (Crocus sativus L.) components in crude plant extract using high-performance liquid chromatography-UV-visible photodiode-array detection-mass spectrometry.
PubMed:Separation of picrocrocin, cis-trans-crocins and safranal of saffron using high-performance liquid chromatography with photodiode-array detection.
 
Notes:
a glucoside of safranal; a bitter-tasting substance. Isol. from saffron (stamens of Crocus sativus). Food colour and flavouring ingredient During the drying process picrocrocin liberates the aglycone (HTCC, C10H16O2) due to the action of the enzyme glucosidase. The aglycone is then transformed to safranal by dehydration. Picrocrocin is a degradation product of the carotenoid zeaxanthin.[citation needed]; Picrocrocin is a glycoside formed from glucose and safranal. It is found in the spice saffron, which comes from the crocus flower. Picrocrocin has a bitter taste and is the chemical most responsible for the taste of saffron.; ; It is believed that picrocrocin is a degradation product of the carotenoid zeaxanthin (Wikipedia).; Picrocrocin is a monoterpene glycoside precursor of safranal. It is found in the spice saffron, which comes from the crocus flower. Picrocrocin has a bitter taste and is the chemical most responsible for the taste of saffron.
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