Record Information
Version1.0
Creation date2010-04-08 22:05:35 UTC
Update date2018-05-28 22:42:58 UTC
Primary IDFDB002944
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCalendic acid
DescriptionIsolated from Calendula officinalis (pot marigold) seed oil Calendic acid (sometimes ?-Calendic acid) is an unsaturated fatty acid, named for the pot marigold (genus Calendula), from which it is obtained. It is chemically similar to the conjugated linoleic acids; laboratory work suggests it may have similar health benefits.; Calendic acid is an omega-6 fatty acid. though not usually listed with this group. Calendic acid (8t,10t,12c-18:3) is synthesised in Calendula officinalis from linoleate (9c,12c-18:2) by an unusual ?12-oleate desaturase (a FAD 2 variant) that converts the cis-double bond in position 9 to a trans,trans-conjugated double bond system (8t,10t). An all-trans beta isomer has been described.
CAS Number28872-28-8
Structure
Thumb
Synonyms
SynonymSource
CalendateGenerator
8E,10E,12Z-Octadecatrienoic acidHMDB
alpha-Calendic acidHMDB
C18:3N-6,8,10HMDB
Calendulic acidHMDB
trans-8, trans-10, cis-12-Octadecatrienoic acidHMDB
8E,10E,12Z-OctadecatrienoateHMDB
a-CalendateHMDB
a-Calendic acidHMDB
alpha-CalendateHMDB
Α-calendateHMDB
Α-calendic acidHMDB
CalendulateHMDB
trans-8, trans-10, cis-12-OctadecatrienoateHMDB
Calendic acidChEBI
trans-8, trans-10, cis-12-octadecatrienoic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP6.66ALOGPS
logP6.06ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)4.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability36 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H30O2
IUPAC name(8E,10E,12Z)-octadeca-8,10,12-trienoic acid
InChI IdentifierInChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10+
InChI KeyDQGMPXYVZZCNDQ-KBPWROHVSA-N
Isomeric SMILESCCCCC\C=C/C=C/C=C/CCCCCCC(O)=O
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
Classification
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.65%; H 10.86%; O 11.49%DFC
Melting PointMp 40-40.5°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9660000000-d828aaab6ed3d3077513View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01yc-9621000000-89f2294fe8e5a7fa99b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0190000000-31cd9fbd0511b99abd28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-5890000000-72f37321b7fde75b1a82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-8930000000-2ae64d84444e7d3105feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f6df0fd86f077c397e84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-74939ebc0a54bce2e7b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-abe728a7db5610480673View in MoNA
ChemSpider ID4445945
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5282818
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30962
CRC / DFC (Dictionary of Food Compounds) IDGZM12-R:CPM05-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCalendic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference