Record Information
Version1.0
Creation date2010-04-08 22:13:25 UTC
Update date2019-11-26 03:15:29 UTC
Primary IDFDB017968
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChlorophyll a
DescriptionIt is used in food processing as an appearance control agent for colours Chlorophyll is a chlorin pigment, which is structurally similar to and produced through the same metabolic pathway as other porphyrin pigments such as heme. At the center of the chlorin ring is a magnesium ion. For the structures depicted in this article, some of the ligands attached to the Mg2+ center are omitted for clarity. The chlorin ring can have several different side chains, usually including a long phytol chain. There are a few different forms that occur naturally, but the most widely distributed form in terrestrial plants is chlorophyll a. The general structure of chlorophyll a was elucidated by Hans Fischer in 1940, and by 1960, when most of the stereochemistry of chlorophyll a was known, Robert Burns Woodward published a total synthesis of the molecule as then known. In 1967, the last remaining stereochemical elucidation was completed by Ian Fleming, and in 1990 Woodward and co-authors published an updated synthesis.; Chlorophyll is a green pigment found in most plants, algae, and cyanobacteria. Its name is derived from the Greek ?????? (chloros "green") and ?????? (phyllon "leaf"). Chlorophyll absorbs light most strongly in the blue and red but poorly in the green portions of the electromagnetic spectrum, hence the green colour of chlorophyll-containing tissues such as plant leaves.; Chlorophyll itself is bound to proteins and can transfer the absorbed energy in the required direction. Protochlorophyllide, differently, mostly occur in the free form and under light conditions act as photosensitizer, forming highly toxic free radicals. Hence plants need an efficient mechanism of regulating the amount of chlorophyll precursor. In angiosperms, this is done at the step of aminolevulinic acid (ALA), one of the intermediate compounds in the biosynthesis pathway. Plants that are fed by ALA accumulate high and toxic levels of protochlorophyllide, so do the mutants with the damaged regulatory system.; Chlorosis is a condition in which leaves produce insufficient chlorophyll, turning them yellow. Chlorosis can be caused by a nutrient deficiency including iron - called iron chlorosis, or in a shortage of magnesium or nitrogen. Soil pH sometimes play a role in nutrient-caused chlorosis, many plants are adapted to grow in soils with specific pHs and their ability to absorb nutrients from the soil can be dependent on the soil pH. Chlorosis can also be caused by pathogens including viruses, bacteria and fungal infections or sap sucking insects.
CAS Number479-61-8
Structure
Thumb
Synonyms
SynonymSource
[3,7,11,15-Tetramethyl-2-hexadecenyl 9-ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoato(2-)-N23,N24,N25,N26]magnesium, 9ciHMDB
[3,7,11,15-Tetramethyl-2-hexadecenyl 9-ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoato(2-)-N23,N24,N25,N26]magnesium, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.00018 g/LALOGPS
logP2.59ALOGPS
logS-6.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area116.26 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity271.81 m³·mol⁻¹ChemAxon
Polarizability109.65 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC55H72MgN4O5
IUPAC name
InChI IdentifierInChI=1S/C55H73N4O5.Mg/c1-13-39-35(8)42-28-44-37(10)41(24-25-48(60)64-27-26-34(7)23-17-22-33(6)21-16-20-32(5)19-15-18-31(3)4)52(58-44)50-51(55(62)63-12)54(61)49-38(11)45(59-53(49)50)30-47-40(14-2)36(9)43(57-47)29-46(39)56-42;/h13,26,28-33,37,41,51H,1,14-25,27H2,2-12H3,(H-,56,57,58,59,61);/q-1;+2/p-1/b34-26-;
InChI KeyATNHDLDRLWWWCB-NOEFFRSSSA-M
Isomeric SMILESCCC1=C(C)C2=[N]3C1=CC1=C(C)C4=C5N1[Mg]31N3C(=CC6=[N]1C(C(CCC(=O)OC\C=C(\C)CCCC(C)CCCC(C)CCCC(C)C)C6C)=C5C(C(=O)OC)C4=O)C(C)=C(C=C)C3=C2
Average Molecular Weight893.489
Monoisotopic Molecular Weight892.535313332
Classification
Description Belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct ParentMetallotetrapyrroles
Alternative Parents
Substituents
  • Metallotetrapyrrole skeleton
  • Diterpenoid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Fatty acyl
  • Pyrrole
  • Pyrroline
  • Heteroaromatic compound
  • Methyl ester
  • Carboxylic acid ester
  • Ketimine
  • Azacycle
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic zwitterion
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Imine
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic salt
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.93%; H 8.12%; Mg 2.72%; N 6.27%; O 8.95%DFC
Melting PointMp 117-120°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -262 (Me2CO)DFC
Spectroscopic UV Data660 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID21427799
ChEMBL IDNot Available
KEGG Compound IDC05306
Pubchem Compound ID45109766
Pubchem Substance IDNot Available
ChEBI ID18230
Phenol-Explorer IDNot Available
DrugBank IDDB02133
HMDB IDHMDB38578
CRC / DFC (Dictionary of Food Compounds) IDLCS34-B:LCS34-B
EAFUS IDNot Available
Dr. Duke IDCHLOROPHYLL-A
BIGG IDNot Available
KNApSAcK IDC00001528
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDChlorophyll_a
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).