Umbellic acid

From Wikipedia, the free encyclopedia

Umbellic acid

IUPAC name (E)-3-(2,4-dihydroxyphenyl)prop-2-enoic acid
Other names 2,4-Dihydroxycinnamic acid (E)-2,4-Dihydroxycinnamic acid (2E)-3-(2,4-Dihydroxyphenyl)acrylic acid
Identifiers
CAS number	614-86-8
PubChem	446611
ChemSpider	393925
Jmol-3D images	Image 1
SMILES C1=CC(=C(C=C1O)O)C=CC(=O)O
InChI InChI=1S/C9H8O4/c10-7-3-1-6(8(11)5-7)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+ Key: HGEFWFBFQKWVMY-DUXPYHPUSA-N
Properties
Molecular formula	C₉H₈O₄
Molar mass	180.16 g mol⁻¹
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.

${\xrightarrow {PAL}}$

${\xrightarrow {C4H}}$

${\xrightarrow {C2H}}$

$\longrightarrow$

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.^[1]

References

↑ Hashidoko, Y; Tanaka, T; Tahara, S (2001). "Induction of 4-hydroxycinnamate decarboxylase in Klebsiella oxytoca cells exposed to substrates and non-substrate 4-hydroxycinnamate analogs". Bioscience, biotechnology, and biochemistry 65 (12): 2604–12. PMID 11826954.

External links

The dictionary definition of umbellic acid at Wiktionary

Types of hydroxycinnamic acids

Aglycones

Precursor	Cinnamic acid

Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid

Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid

Trihydroxycinnamic acids	3,4,6-Trihydroxycinnamic acid

O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Sinapinic acid

others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid

esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Ferulic acid glucoside
p-Coumaric acid glucoside
1-Sinapoyl-D-glucose

Tartaric acid esters

Caftaric acid
Cichoric acid (Dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid

Ethyl caffeate
Methyl caffeate
CAPE (Caffeic acid phenethyl ester)
Rosmarinic acid (ester with 3,4-dihydroxyphenyl lactic acid)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5'-Diferulic acid, 8-O-4'-Diferulic acid, 8,5'-Diferulic acid, 8,5'-DiFA (DC), 8,5'-DiFA (BF), 8,8'-Diferulic acid

Trimers	Triferulic acids : 5-5',8'-O-4"-Triferulic acid

Tetramers	Tetraferulic acids

Conjugates with coenzyme A

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.