picrocrocin

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

CAS: 138-55-6 C16 H26 O7 MW: 330.37762000

Identification

Namepicrocrocin
IUPAC(4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde
CAS Number138-55-6
FDA UNIION5B022511
Molecular FormulaC16 H26 O7
Molecular Weight330.37762000
Nikkaji NumberJ5.635I

Regulatory

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)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for picrocrocin usage levels up tonot for fragrance use.
Recommendation for picrocrocin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

saffron flower saffron oil saffron stigma saffron tissue culture

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 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.