Umbelliferone

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Umbelliferone
Chemical structure of umbelliferone
Unbelliferone, or 7-hydroxycoumarin, is a yellowish white crystalline powder lacking the odor of coumarin, or any strong odor.
Names
Preferred IUPAC name
7-Hydroxy-2H-1-benzopyran-2-one
Other names
7-hydroxycoumarin, hydrangine, skimmetine, beta-umbelliferone
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.002.038 Edit this at Wikidata
UNII
  • InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H checkY
    Key: ORHBXUUXSCNDEV-UHFFFAOYSA-N checkY
  • InChI=1/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
    Key: ORHBXUUXSCNDEV-UHFFFAOYAL
  • c1cc(cc2c1ccc(=O)o2)O
Properties
C9H6O3
Molar mass 162.14 g/mol
Appearance yellowish-white crystalline odorless powder
Melting point 230 °C (446 °F; 503 K) (decomposes)
-88.22·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and beta-umbelliferone, is a natural product of the coumarin family.

It absorbs

antimutagenic,[1] it is used in sunscreens.[2] Umbelliferone has been reported to have antioxidant properties.[3][4]

It is a yellowish-white crystalline solid that has a slight solubility in hot water, but high solubility in ethanol.

Natural occurrences and name

Umbelliferone's name is from the

umbelliferae family of plants, and the plant family in turn was named for their umbrella-shaped inflorescences, each called an umbel
.

Umbelliferone occurs in many familiar plants from the

Hieracium pilosella, Asteraceae) or the bigleaf hydrangea (Hydrangea macrophylla
, Hydrangeaceae, under the name hydrangine).

It is one of the components of asafoetida, the dried latex from the giant fennel (Ferula communis).

It is also found in

Justicia pectoralis (Acanthaceae).[5][6]

Biosynthesis

Umbelliferone is a

4-coumaric acid. The 4-coumaric acid is again hydroxylated by cinnamate/coumarate 2-hydroxylase to yield 2,4-dihydroxy-cinnamic acid (umbellic 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   Cinnamic acid  para-Coumaric acid  2,4-Dihydroxycinnamic acid  Umbelliferone

Chemical synthesis

Umbelliferone is traditionally synthesized using the Pechmann condensation, from resorcinol and formylacetic acid (generated from malic acid in situ).[7]

The Pechmann condensation as applied to umbelliferone
The Pechmann condensation as applied to umbelliferone

A newer synthesis uses

catalyst
.

Ultraviolet fluorescence

Umbelliferone absorbs strongly at 300, 305 and 325

hydroxyl group is deprotonated (pKa
= 7.7).

Uses

The ultraviolet activity of umbelliferone led to its use as a

gain medium for dye lasers. Umbelliferone can be used as a fluorescence indicator for metal ions such as copper and calcium. It acts as a pH indicator in the range 6.5-8.9.[citation needed
]

Umbelliferone is a potent inhibitor of type 3

17β-hydroxysteroid dehydrogenase, the primary enzyme responsible for the conversion of 4-androstene-3,17-dione to testosterone, with IC50 of 1.4 μM.[8]

Derivatives

Umbelliferone is the parent compound for a large number of natural products.

furocoumarins such as marmesin, angelicin, and psoralen
.

Herniarin and marmin, umbelliferone derivatives

Umbelliferone 7-apiosylglucoside can be isolated from the root of Gmelina arborea.[9]

See also

References

  1. PMID 6403855
    .
  2. PMID 19081820
    .
  3. ^ "UMBELLIFERONE". www.chemicalland21.com. Retrieved 21 November 2011.
  4. PMID 26244074
    .
  5. PMID 10771205
    .
  6. S2CID 84525194. Archived from the original
    on 2013-01-05. Retrieved 2010-06-26.
  7. ISBN 978-81-88237-33-3
    .
  8. PMID 12570693
    .
  9. doi:10.1016/S0031-9422(00)82575-3
    .

Further reading

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Umbelliferone&oldid=1211526279"