Phaseic acid

Phaseic acid

Names
IUPAC name (2Z,4E)-5-[(1R,5R,8S)-8-hydroxy-1, 5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2, 4-dienoic acid
Other names Phaseic acid
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28205 N
ChemSpider	4444860 N
KEGG	C09707 N
PubChem CID	5281527
InChI InChI=1S/C15H20O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-/t13-,14-,15+/m1/s1 N Key: IZGYIFFQBZWOLJ-UUZREKTLSA-N N InChI=1/C15H20O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-/t13-,14-,15+/m1/s1 Key: IZGYIFFQBZWOLJ-UUZREKTLBL
SMILES CC(\C=C[C@]1(O)[C@@]2(C)CO[C@]1(C)CC(=O)C2)=C\C(O)=O
Properties
Chemical formula	C15H20O5
Molar mass	280.31 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,

Phaseic acid is a terpenoid catabolite of abscisic acid. Like abscisic acid, it is a plant hormone associated with photosynthesis arrest and abscission.

Abscisic acid (ABA) is a multifunctional plant hormone, playing roles in germination, seasonal growth patterns, and stress response. ABA levels are believed to be regulated in part by control of ABA catabolism, specifically by oxidation to form phaseic acid. Phaseic acid can therefore be thought of as a degradation product of ABA, although it may have other functions. The introduction of high phaseic acid concentrations have been found to impede stomatal closure and reduce photosynthesis in arabidopsis but this may be a result of product inhibition rather than recognition of phaseic acid by a receptor.

Phaseic acid inhibits glutamate receptors in mouse brain.

Phaseic acid is an isoprenoid, which means that it is derived from isoprene units. The activated terpene geranylgeranyl pyrophosphate is combined with itself to produce the common carotenoid precursor, lycopene.

Phaseic acid is a product of abscisic acid, which is itself the product of the C₄₀carotenoid zeaxanthin via at least four enzymatic steps. Zeaxanthin is epoxidized to form violaxanthin or neoxanthin. The C₁₅ end of the molecule is then cleaved by an epoxycarotenoid epoxygenase to form xanthoxin, an aldehyde.