Showing Compound Picrocrocin (FDB014885)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:31 UTC

Update date

2019-11-26 03:10:52 UTC

Primary ID

FDB014885

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Picrocrocin

Description

Isolated 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 .; 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.

CAS Number

138-55-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	8.04 g/L	ALOGPS
logP	-0.57	ALOGPS
logP	-0.75	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.18 m³·mol⁻¹	ChemAxon
Polarizability	34.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H26O7

IUPAC name

2,6,6-trimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-1-ene-1-carbaldehyde

InChI Identifier

InChI=1S/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3

InChI Key

WMHJCSAICLADIN-UHFFFAOYSA-N

Isomeric SMILES

CC1=C(C=O)C(C)(C)CC(C1)OC1OC(CO)C(O)C(O)C1O

Average Molecular Weight

330.3734

Monoisotopic Molecular Weight

330.167853186

Classification

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Monosaccharide
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aldehyde
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

an apocarotenoid (CPD-8668 )
a glucoside (CPD-8668 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 58.17%; H 7.93%; O 33.90%	DFC
Melting Point	Mp 156°	DFC
Optical Rotation	[a]20D -58 (H2O)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0i0r-0904000000-8640d3381d1f16d4fd87	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-1900000000-d1c75685a5ea9420dd50	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v09-2900000000-c3e5455aa6a5d3216102	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00or-1917000000-0bdf6a85b6282b0a7107	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1901000000-d97fa0dfe220b9df0fa8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-3900000000-3215b45b7b07963484f7	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

17216348

ChEMBL ID

Not Available

KEGG Compound ID

C17055

Pubchem Compound ID

22833654

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05796

CRC / DFC (Dictionary of Food Compounds) ID

JPV04-Y:JXD64-I

EAFUS ID

Not Available

Dr. Duke ID

PICROCROCIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Picrocrocin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Show entries

Search:

Showing 1 to 1 of 1 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Picrocrocin (FDB014885)

Structure for FDB014885 (Picrocrocin)