Actions

::Umbellic acid

::concepts



Umbellic acid
colspan=2 style="background:#f8eaba; text-align:center;" Names
colspan=2 style="background:#f8eaba; text-align:center;" Identifiers{{#invoke:TemplatePar check template=Template:Chembox Identifiers opt=

3DMet= ATCCode= ATCCode_prefix= ATCCode_suffix= ATC_Supplemental= ATCvet= Abbreviations= Beilstein= CASNo1= CASNo1_Comment= CASNo1_Ref= CASNo2= CASNo2_Comment= CASNo2_Ref= CASNo3= CASNo3_Comment= CASNo3_Ref= CASNo4= CASNo4_Comment= CASNo4_Ref= CASNo5= CASNo5_Comment= CASNo5_Ref= CASNo= CASNoOther= CASNo_Comment= CASNo_Ref= ChEBI1= ChEBI1_Comment= ChEBI1_Ref= ChEBI2= ChEBI2_Comment= ChEBI2_Ref= ChEBI3= ChEBI3_Comment= ChEBI3_Ref= ChEBI4= ChEBI4_Comment= ChEBI4_Ref= ChEBI5= ChEBI5_Comment= ChEBI5_Ref= ChEBI= ChEBIOther= ChEBI_Comment= ChEBI_Ref= ChEMBL1= ChEMBL1_Comment= ChEMBL1_Ref= ChEMBL2= ChEMBL2_Comment= ChEMBL2_Ref= ChEMBL3= ChEMBL3_Comment= ChEMBL3_Ref= ChEMBL4= ChEMBL4_Comment= ChEMBL4_Ref= ChEMBL5= ChEMBL5_Comment= ChEMBL5_Ref= ChEMBL= ChEMBLOther= ChEMBL_Comment= ChEMBL_Ref= ChemSpiderID1= ChemSpiderID1_Comment= ChemSpiderID1_Ref= ChemSpiderID2= ChemSpiderID2_Comment= ChemSpiderID2_Ref= ChemSpiderID3= ChemSpiderID3_Comment= ChemSpiderID3_Ref= ChemSpiderID4= ChemSpiderID4_Comment= ChemSpiderID4_Ref= ChemSpiderID5= ChemSpiderID5_Comment= ChemSpiderID5_Ref= ChemSpiderID= ChemSpiderIDOther= ChemSpiderID_Comment= ChemSpiderID_Ref= DrugBank1= DrugBank1_Comment= DrugBank1_Ref= DrugBank2= DrugBank2_Comment= DrugBank2_Ref= DrugBank3= DrugBank3_Comment= DrugBank3_Ref= DrugBank4= DrugBank4_Comment= DrugBank4_Ref= DrugBank5= DrugBank5_Comment= DrugBank5_Ref= DrugBank= DrugBankOther= DrugBank_Comment= DrugBank_Ref= EC number= EC number_Comment= EC_number= EC_number_Comment= EINECS= Gmelin= IUPHAR_ligand= IUPHAR_ligand1= IUPHAR_ligand2= IUPHAR_ligand3= IUPHAR_ligand4= IUPHAR_ligand5= IUPHAR_ligand_Comment= IUPHAR_ligand1_Comment= IUPHAR_ligand2_Comment= IUPHAR_ligand3_Comment= IUPHAR_ligand4_Comment= IUPHAR_ligand5_Comment= IUPHAR_ligand_Other= InChI1= InChI1_Comment= InChI1_Ref= InChI2= InChI2_Comment= InChI2_Ref= InChI3= InChI3_Comment= InChI3_Ref= InChI4= InChI4_Comment= InChI4_Ref= InChI5= InChI5_Comment= InChI5_Ref= InChI= InChIKey1= InChIKey1_Ref= InChIKey2= InChIKey2_Ref= InChIKey3= InChIKey3_Ref= InChIKey4= InChIKey4_Ref= InChIKey5= InChIKey5_Ref= InChIKey= InChIKey_Ref= InChIOther= InChI_Comment= InChI_Ref= JmolOther= KEGG1= KEGG1_Comment= KEGG1_Ref= KEGG2= KEGG2_Comment= KEGG2_Ref= KEGG3= KEGG3_Comment= KEGG3_Ref= KEGG4= KEGG4_Comment= KEGG4_Ref= KEGG5= KEGG5_Comment= KEGG5_Ref= KEGG= KEGGOther= KEGG_Comment= KEGG_Ref= MeSHName= PubChem1= PubChem1_Comment= PubChem2= PubChem2_Comment= PubChem3= PubChem3_Comment= PubChem4= PubChem4_Comment= PubChem5= PubChem5_Comment= PubChem= PubChemOther= PubChem_Comment= RTECS= SMILES1= SMILES1_Comment= SMILES2= SMILES2_Comment= SMILES3= SMILES3_Comment= SMILES4= SMILES4_Comment= SMILES5= SMILES5_Comment= SMILESOther= SMILES= SMILES_Comment= StdInChI= StdInChIKey= StdInChIKey_Ref= StdInChI_Comment= StdInChI_Ref= UNII= UNII1= UNII1_Comment= UNII1_Ref= UNII2= UNII2_Comment= UNII2_Ref= UNII3= UNII3_Comment= UNII3_Ref= UNII4= UNII4_Comment= UNII4_Ref= UNII5= UNII5_Comment= UNII5_Ref= UNIIOther= UNII_Comment= UNII_Ref= UNNumber=

cat=Chemical articles with unknown parameter in Chembox preview=
@@@
This error is harmless. The message shows only in Preview, it will not show after Save.
|errNS=0}}
ChemSpider
{{safesubst:#invoke:collapsible list|main}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
{{#invoke:TemplatePar

|check |template=Template:Chembox |all= |opt= IUPACNames= IUPACName= ImageAlt1= ImageAlt2= ImageAlt3= ImageAlt4= ImageAltL1= ImageAltL2= ImageAltL3= ImageAltL4= ImageAltR1= ImageAltR2= ImageAltR3= ImageAltR4= ImageAlt= ImageCaption1= ImageCaption2= ImageCaption3= ImageCaption4= ImageCaptionL1= ImageCaptionL2= ImageCaptionL3= ImageCaptionL4= ImageCaptionR1= ImageCaptionR2= ImageCaptionR3= ImageCaptionR4= ImageCaption= ImageFile1_Ref= ImageFile1= ImageFile2_Ref= ImageFile2= ImageFile3_Ref= ImageFile3= ImageFile4_Ref= ImageFile4= ImageFileL1_Ref= ImageFileL1= ImageFileL2_Ref= ImageFileL2= ImageFileL3_Ref= ImageFileL3= ImageFileL4_Ref= ImageFileL4= ImageFileR1_Ref= ImageFileR1= ImageFileR2_Ref= ImageFileR2= ImageFileR3_Ref= ImageFileR3= ImageFileR4_Ref= ImageFileR4= ImageFile_Ref= ImageFile= ImageName1= ImageName2= ImageName3= ImageName4= ImageNameL1= ImageNameL2= ImageNameL3= ImageNameL4= ImageNameR1= ImageNameR2= ImageNameR3= ImageNameR4= ImageName= ImageSize1= ImageSize2= ImageSize3= ImageSize4= ImageSizeL1= ImageSizeL2= ImageSizeL3= ImageSizeL4= ImageSizeR1= ImageSizeR2= ImageSizeR3= ImageSizeR4= ImageSize= Name= OtherNames= PIN= Reference= Section1= Section2= Section3= Section4= Section5= Section6= Section7= Section8= Section9= SystematicName= Verifiedfields= Watchedfields= verifiedrevid= Verifiedimages= general_note= show_infobox_ref= show_ss_note= style-left-column-width= style= width |cat=Chemical articles with unknown parameter in Chembox

|format=0|preview=
@@@
This error is harmless. The message shows only in Preview, it will not show after Save.
|errNS=0}}

Umbellic acid (2,4-dihydroxycinnamic acid) is a hydroxycinnamic acid. It is an isomer of caffeic acid.

It is a precursor in the umbelliferone biosynthesis pathway. Umbelliferone is a phenylpropanoid and as such is synthesized from L-phenylalanine, which in turn is produced via the shikimate pathway. Phenylalanine is lysated into cinnamic acid, followed by hydroxylation by cinnamate 4-hydroxylase to yield 4-coumaric acid. The 4-coumaric acid is again hydroxylated by cinnamate/coumarate 2-hydroxylase to yield 2,4-dihydroxy-cinnamic acid followed by a bond rotation of the unsaturated bond adjacent to the carboxylic acid group. Finally an intramolecular attack from the hydroxyl group of C2' to the carboxylic acid group closes the ring and forms the lactone umbelliferone.

L-phenylalanine  <math>\xrightarrow{PAL}</math> Cinnamic acid <math>\xrightarrow{C4H}</math> para-Coumaric acid <math>\xrightarrow{C2H}</math> 2,4-Dihydroxycinnamic acid <math>\longrightarrow</math> Umbelliferone

The enzyme 4-hydroxycinnamate decarboxylase, induced in bacteria species such as Klebsiella oxytoca, works also with p-coumaric acid analogs such as E-2,4-dihydroxycinnamic acid.<ref>{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref>


Umbellic acid sections
Intro   References    External links   

PREVIOUS: IntroNEXT: References
<<>>

Image::chembox    Group::first    ''E''::section    Small::pathway    Journal::cinnamic    Followed::analogs

Umbellic acid
colspan=2 style="background:#f8eaba; text-align:center;" Names
colspan=2 style="background:#f8eaba; text-align:center;" Identifiers{{#invoke:TemplatePar check template=Template:Chembox Identifiers opt=

3DMet= ATCCode= ATCCode_prefix= ATCCode_suffix= ATC_Supplemental= ATCvet= Abbreviations= Beilstein= CASNo1= CASNo1_Comment= CASNo1_Ref= CASNo2= CASNo2_Comment= CASNo2_Ref= CASNo3= CASNo3_Comment= CASNo3_Ref= CASNo4= CASNo4_Comment= CASNo4_Ref= CASNo5= CASNo5_Comment= CASNo5_Ref= CASNo= CASNoOther= CASNo_Comment= CASNo_Ref= ChEBI1= ChEBI1_Comment= ChEBI1_Ref= ChEBI2= ChEBI2_Comment= ChEBI2_Ref= ChEBI3= ChEBI3_Comment= ChEBI3_Ref= ChEBI4= ChEBI4_Comment= ChEBI4_Ref= ChEBI5= ChEBI5_Comment= ChEBI5_Ref= ChEBI= ChEBIOther= ChEBI_Comment= ChEBI_Ref= ChEMBL1= ChEMBL1_Comment= ChEMBL1_Ref= ChEMBL2= ChEMBL2_Comment= ChEMBL2_Ref= ChEMBL3= ChEMBL3_Comment= ChEMBL3_Ref= ChEMBL4= ChEMBL4_Comment= ChEMBL4_Ref= ChEMBL5= ChEMBL5_Comment= ChEMBL5_Ref= ChEMBL= ChEMBLOther= ChEMBL_Comment= ChEMBL_Ref= ChemSpiderID1= ChemSpiderID1_Comment= ChemSpiderID1_Ref= ChemSpiderID2= ChemSpiderID2_Comment= ChemSpiderID2_Ref= ChemSpiderID3= ChemSpiderID3_Comment= ChemSpiderID3_Ref= ChemSpiderID4= ChemSpiderID4_Comment= ChemSpiderID4_Ref= ChemSpiderID5= ChemSpiderID5_Comment= ChemSpiderID5_Ref= ChemSpiderID= ChemSpiderIDOther= ChemSpiderID_Comment= ChemSpiderID_Ref= DrugBank1= DrugBank1_Comment= DrugBank1_Ref= DrugBank2= DrugBank2_Comment= DrugBank2_Ref= DrugBank3= DrugBank3_Comment= DrugBank3_Ref= DrugBank4= DrugBank4_Comment= DrugBank4_Ref= DrugBank5= DrugBank5_Comment= DrugBank5_Ref= DrugBank= DrugBankOther= DrugBank_Comment= DrugBank_Ref= EC number= EC number_Comment= EC_number= EC_number_Comment= EINECS= Gmelin= IUPHAR_ligand= IUPHAR_ligand1= IUPHAR_ligand2= IUPHAR_ligand3= IUPHAR_ligand4= IUPHAR_ligand5= IUPHAR_ligand_Comment= IUPHAR_ligand1_Comment= IUPHAR_ligand2_Comment= IUPHAR_ligand3_Comment= IUPHAR_ligand4_Comment= IUPHAR_ligand5_Comment= IUPHAR_ligand_Other= InChI1= InChI1_Comment= InChI1_Ref= InChI2= InChI2_Comment= InChI2_Ref= InChI3= InChI3_Comment= InChI3_Ref= InChI4= InChI4_Comment= InChI4_Ref= InChI5= InChI5_Comment= InChI5_Ref= InChI= InChIKey1= InChIKey1_Ref= InChIKey2= InChIKey2_Ref= InChIKey3= InChIKey3_Ref= InChIKey4= InChIKey4_Ref= InChIKey5= InChIKey5_Ref= InChIKey= InChIKey_Ref= InChIOther= InChI_Comment= InChI_Ref= JmolOther= KEGG1= KEGG1_Comment= KEGG1_Ref= KEGG2= KEGG2_Comment= KEGG2_Ref= KEGG3= KEGG3_Comment= KEGG3_Ref= KEGG4= KEGG4_Comment= KEGG4_Ref= KEGG5= KEGG5_Comment= KEGG5_Ref= KEGG= KEGGOther= KEGG_Comment= KEGG_Ref= MeSHName= PubChem1= PubChem1_Comment= PubChem2= PubChem2_Comment= PubChem3= PubChem3_Comment= PubChem4= PubChem4_Comment= PubChem5= PubChem5_Comment= PubChem= PubChemOther= PubChem_Comment= RTECS= SMILES1= SMILES1_Comment= SMILES2= SMILES2_Comment= SMILES3= SMILES3_Comment= SMILES4= SMILES4_Comment= SMILES5= SMILES5_Comment= SMILESOther= SMILES= SMILES_Comment= StdInChI= StdInChIKey= StdInChIKey_Ref= StdInChI_Comment= StdInChI_Ref= UNII= UNII1= UNII1_Comment= UNII1_Ref= UNII2= UNII2_Comment= UNII2_Ref= UNII3= UNII3_Comment= UNII3_Ref= UNII4= UNII4_Comment= UNII4_Ref= UNII5= UNII5_Comment= UNII5_Ref= UNIIOther= UNII_Comment= UNII_Ref= UNNumber=

cat=Chemical articles with unknown parameter in Chembox preview=
@@@
This error is harmless. The message shows only in Preview, it will not show after Save.
|errNS=0}}
ChemSpider
{{safesubst:#invoke:collapsible list|main}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
{{#invoke:TemplatePar

|check |template=Template:Chembox |all= |opt= IUPACNames= IUPACName= ImageAlt1= ImageAlt2= ImageAlt3= ImageAlt4= ImageAltL1= ImageAltL2= ImageAltL3= ImageAltL4= ImageAltR1= ImageAltR2= ImageAltR3= ImageAltR4= ImageAlt= ImageCaption1= ImageCaption2= ImageCaption3= ImageCaption4= ImageCaptionL1= ImageCaptionL2= ImageCaptionL3= ImageCaptionL4= ImageCaptionR1= ImageCaptionR2= ImageCaptionR3= ImageCaptionR4= ImageCaption= ImageFile1_Ref= ImageFile1= ImageFile2_Ref= ImageFile2= ImageFile3_Ref= ImageFile3= ImageFile4_Ref= ImageFile4= ImageFileL1_Ref= ImageFileL1= ImageFileL2_Ref= ImageFileL2= ImageFileL3_Ref= ImageFileL3= ImageFileL4_Ref= ImageFileL4= ImageFileR1_Ref= ImageFileR1= ImageFileR2_Ref= ImageFileR2= ImageFileR3_Ref= ImageFileR3= ImageFileR4_Ref= ImageFileR4= ImageFile_Ref= ImageFile= ImageName1= ImageName2= ImageName3= ImageName4= ImageNameL1= ImageNameL2= ImageNameL3= ImageNameL4= ImageNameR1= ImageNameR2= ImageNameR3= ImageNameR4= ImageName= ImageSize1= ImageSize2= ImageSize3= ImageSize4= ImageSizeL1= ImageSizeL2= ImageSizeL3= ImageSizeL4= ImageSizeR1= ImageSizeR2= ImageSizeR3= ImageSizeR4= ImageSize= Name= OtherNames= PIN= Reference= Section1= Section2= Section3= Section4= Section5= Section6= Section7= Section8= Section9= SystematicName= Verifiedfields= Watchedfields= verifiedrevid= Verifiedimages= general_note= show_infobox_ref= show_ss_note= style-left-column-width= style= width |cat=Chemical articles with unknown parameter in Chembox

|format=0|preview=
@@@
This error is harmless. The message shows only in Preview, it will not show after Save.
|errNS=0}}

Umbellic acid (2,4-dihydroxycinnamic acid) is a hydroxycinnamic acid. It is an isomer of caffeic acid.

It is a precursor in the umbelliferone biosynthesis pathway. Umbelliferone is a phenylpropanoid and as such is synthesized from L-phenylalanine, which in turn is produced via the shikimate pathway. Phenylalanine is lysated into cinnamic acid, followed by hydroxylation by cinnamate 4-hydroxylase to yield 4-coumaric acid. The 4-coumaric acid is again hydroxylated by cinnamate/coumarate 2-hydroxylase to yield 2,4-dihydroxy-cinnamic acid followed by a bond rotation of the unsaturated bond adjacent to the carboxylic acid group. Finally an intramolecular attack from the hydroxyl group of C2' to the carboxylic acid group closes the ring and forms the lactone umbelliferone.

L-phenylalanine  <math>\xrightarrow{PAL}</math> Cinnamic acid <math>\xrightarrow{C4H}</math> para-Coumaric acid <math>\xrightarrow{C2H}</math> 2,4-Dihydroxycinnamic acid <math>\longrightarrow</math> Umbelliferone

The enzyme 4-hydroxycinnamate decarboxylase, induced in bacteria species such as Klebsiella oxytoca, works also with p-coumaric acid analogs such as E-2,4-dihydroxycinnamic acid.<ref>{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref>


Umbellic acid sections
Intro   References    External links   

PREVIOUS: IntroNEXT: References
<<>>