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H24003

Sigma-Aldrich

Umbelliferone

99%

Synonym(s):

7-Hydroxy-2H-1-benzopyran-2-one, 7-Hydroxycoumarin

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About This Item

Empirical Formula (Hill Notation):
C9H6O3
CAS Number:
93-35-6
Molecular Weight:
162.14
Beilstein:
127683
EC Number:
202-240-3
MDL number:
MFCD00006878
UNSPSC Code:
12352100
PubChem Substance ID:
24895162
NACRES:
NA.22
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Quality Level

100

Assay

99%

mp

230 °C (dec.) (lit.)

solubility

dioxane: soluble
ethanol: soluble

SMILES string

Oc1ccc2C=CC(=O)Oc2c1

InChI

1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H

InChI key

ORHBXUUXSCNDEV-UHFFFAOYSA-N

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Application

Umbelliferone can be used:
  • To synthesize fluorescent probes to detect cyanide anions in water at biological pH[1] and for in vitro and in vivo detection of hydrogen peroxide.[2]
  • In the preparation of coumarin-based polymer as optical data storage material.[3]
  • As a precursor to synthesize novobiocin derivatives that exhibit antibacterial agents as well as inhibitors of DNA gyrase.[4]
  • As the starting material to synthesize (+)-decursinol[5] and (+)-angelmarin.[6]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM5153
BCCL7215
BCCH6868
BCCJ0548
BCCG7078

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Reversible two-photon optical data storage in coumarin-based copolymers.
Iliopoulos K, et al.
Journal of the American Chemical Society, 132(41), 14343-14345 (2010)
Fluorescent chemodosimeter for selective detection of cyanide in water.
Lee K S, et al.
Organic Letters, 10(1), 49-51 (2008)
Total synthesis of (+)-angelmarin.
Magolan J and Coster M J
The Journal of Organic Chemistry, 74(14), 5083-5086 (2009)
Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore.
Du L, et al.
Tetrahedron Letters, 49(19), 3045-3048 (2008)
Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90.
Burlison J A, et al.
Journal of the American Chemical Society, 128(48), 15529-15536 (2006)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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