Showing Compound Umbelliferone (FDB001094)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:50 UTC

Update date

2025-11-18 22:28:00 UTC

Primary ID

FDB001094

Secondary Accession Numbers

FDB012649

Chemical Information

FooDB Name

Umbelliferone

Description

Umbelliferone, also known as 7-hydroxycoumarin or hydrangin, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Umbelliferone is found, on average, in the highest concentration within anises (Pimpinella anisum) and beer. Umbelliferone has also been detected, but not quantified in, several different foods, such as ryes (Secale cereale), durians (Durio zibethinus), allspices (Pimenta dioica), japanese pumpkins (Cucurbita maxima), and garden onion (var.). This could make umbelliferone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Umbelliferone.

CAS Number

93-35-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
7-Hydroxy-2H-1-benzopyran-2-one	ChEBI
7-Hydroxycoumarin	ChEBI
beta-Umbelliferone	ChEBI
Hydrangin	ChEBI
Skimmetin	ChEBI
b-Umbelliferone	Generator
Β-umbelliferone	Generator
7-Hydroxy-2H-chromen-2-one	HMDB
7-Hydroxy-coumarin	HMDB
7-Hydroxycoumarin sulfate	HMDB, MeSH
7-Hydroxycoumarin sulphate	HMDB
7-Hydroxycoumarin, 14C-labeled	HMDB, MeSH
7-Oxycoumarin	HMDB
beta -Umbelliferone	HMDB
Hydrangine	HMDB
Skimmetine	HMDB
Umbelliferon	HMDB
Umbelliferone (hydrangin, skimmetin)	HMDB
β-umbelliferone	biospider
2H-1-Benzopyran-2-one, 7-hydroxy-	biospider
7-hydroxycoumarin sulfate	biospider
7-hydroxycoumarin, 14C-labeled	biospider
Beta-umbelliferone	biospider
Coumarin, 7-hydroxy-	biospider
Umbelliferone	db_source
β-umbelliferone	Generator

Predicted Properties

Property	Value	Source
Water Solubility	4.38 g/L	ALOGPS
logP	1.85	ALOGPS
logP	1.48	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	7.84	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.53 m³·mol⁻¹	ChemAxon
Polarizability	15.37 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H6O3

IUPAC name

7-hydroxy-2H-chromen-2-one

InChI Identifier

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

Isomeric SMILES

OC1=CC2=C(C=C1)C=CC(=O)O2

Average Molecular Weight

162.144

Monoisotopic Molecular Weight

162.031694053

Classification

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:27510 )
coumarins (C09315 )
a coumarin (CPD-8186 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 66.67%; H 3.73%; O 29.60%	DFC
Melting Point	Mp 230-232° (223-224°, 227-228°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa1 7.7	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	[base] lmax 377 () (NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03e9-6900000000-0be270410ca1ed2de531	2015-03-01	View Spectrum
GC-MS	Umbelliferone, non-derivatized, GC-MS Spectrum	splash10-03gi-9700000000-61b0cf13acd34fc7ef62	Spectrum
GC-MS	Umbelliferone, non-derivatized, GC-MS Spectrum	splash10-03di-6900000000-dedc215fac13e97ee769	Spectrum
GC-MS	Umbelliferone, non-derivatized, GC-MS Spectrum	splash10-03gi-9700000000-61b0cf13acd34fc7ef62	Spectrum
GC-MS	Umbelliferone, non-derivatized, GC-MS Spectrum	splash10-03di-6900000000-dedc215fac13e97ee769	Spectrum
Predicted GC-MS	Umbelliferone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02ai-0900000000-0624e9db800b4bf28fbb	Spectrum
Predicted GC-MS	Umbelliferone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-5940000000-389049e95813b961c56b	Spectrum
Predicted GC-MS	Umbelliferone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0kmi-0920000000-2cd49ad40f2f08fee3ab	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0kmi-0920000000-2cd49ad40f2f08fee3ab	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0kmi-0920000000-2cd49ad40f2f08fee3ab	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0kmi-0920000000-2cd49ad40f2f08fee3ab	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-03di-0900000000-1c416a1d92a90a4424ff	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-03e9-0900000000-ceab22ae6ab894db98ee	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0900000000-9f3b0c63320b7a16d26f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-03di-0900000000-26b715dfa168a96a7f79	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-03di-0900000000-1349a86992b0b49b6c46	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-03di-0900000000-a4062ec204d8a8bbf557	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-03e9-0900000000-1243c09e68f71ea9dbc9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-a0363e87c8dfdf5684e1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-ef5555622fcf5901817a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-01q9-0900000000-0a23407c9d3acb3a9646	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0089-3900000000-b06b1adaffe70bae6829	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0900000000-18c4c14a01ab29d764d2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0900000000-f9da00f6ddcb61b14a8c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-03e9-0900000000-ceab22ae6ab894db98ee	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0900000000-9f3b0c63320b7a16d26f	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-bafe152884074efd6ae4	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-ba2ab3999b706f4fba94	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-3900000000-94ba274c0fe68fcd5545	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-a37e719efb7afa07f707	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-a5780fb402be64e17c80	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3900000000-f5ab2c793215524c01ec	2016-08-03	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

27510

Phenol-Explorer ID

641

DrugBank ID

Not Available

HMDB ID

HMDB29865

CRC / DFC (Dictionary of Food Compounds) ID

BSX04-T:BSX04-T

EAFUS ID

Not Available

Dr. Duke ID

UMBELLIFERONE

BIGG ID

Not Available

KNApSAcK ID

C00002503

HET ID

07L

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Umbelliferone

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Allelochemic		A chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti-edemic		An agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.	DUKE
Anti histaminic	37956	An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti mitotic		An agent that inhibits mitosis, or cell division, playing a crucial role in regulating cell growth. Therapeutically, it is used to treat cancer by blocking tumor cell proliferation. Key medical uses include chemotherapy for various cancers, such as breast, lung, and colon cancer, to prevent cancer cell division and growth.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Anti prostaglandin	49020	An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-spasmodic	52217	An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.	DUKE
Anti-staphylococcic	33282	An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Candidicide		An agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.	DUKE
Choleretic		An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Lipoxygenase inhibitor	35856	An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Photoactive		A compound that responds to light, often used in photodynamic therapy to treat cancer and skin disorders, with applications in wound healing, antimicrobial treatments, and diagnostic imaging, by triggering chemical reactions upon exposure to sunlight or ultraviolet radiation.	DUKE
Sunscreen	52217	A topical agent that blocks UV radiation, preventing skin damage and reducing the risk of skin cancer. Its therapeutic applications include protection against sunburn, photoaging, and photodermatoses. Key medical uses include prevention of melanoma, basal cell carcinoma, and squamous cell carcinoma, as well as management of photosensitive disorders.	DUKE
Xanthine oxidase inhibitor	35634	An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.	DUKE