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Umbelliferone

$45

  • Brand : BIOFRON

  • Catalogue Number : AV-P11412

  • Specification : 98%

  • CAS number : 93-35-6

  • Formula : C9H6O3

  • Molecular Weight : 162.14

  • PUBCHEM ID : 5281426

  • Volume : 100mg

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Catalogue Number

AV-P11412

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

162.14

Appearance

White crystalline powder

Botanical Source

Calendula officinalis L./Occurs widely in plants including Angelica, Artemisia, Ferula and Ruta spp., Hieracium pilosella, Coronilla varia, Picea abies, Peddiea fischeri, Lepidophyllum cupressiforme, Cymbopogon parkeri, Wikstroemia elliptica, Euphorbia humifusa,

Structure Type

Coumarins

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=CC2=C1C=CC(=O)O2)O

Synonyms

UMBELLIFERON/2H-1-Benzopyran-2-one, 7-hydroxy-/Hydrangine/Umbelliferone/Hydramgin/7-Hydroxy-2H-chromen-2-one/Dichrin A/7-hydroxy-2H-1-benzopyran-2-one/Skimmetine/umberlliferone/SKIMMETIN/7-Hydroxycoumarin/7-hydroxy-coumarin/7-hydroxy-coumarine/hydrangin/7 HC

IUPAC Name

7-hydroxychromen-2-one

Density

1.4±0.1 g/cm3

Solubility

Methanol

Flash Point

181.2±19.3 °C

Boiling Point

382.1±37.0 °C at 760 mmHg

Melting Point

230 °C (dec.)(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:93-35-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30439620

Abstract

Inspired by the recently discovered phenomenon of “horizontal natural product transfer” we investigated the putative uptake of phenolic specialized metabolites. Umbelliferone was chosen for this case study, since this coumarin as well as its derivatives can easily be determined by HPLC analyses. Barley (Hordeum vulgare L.), radish (Raphanus sativus L.), pea (Pisum sativum L.), flax (Linum usitatissimum L.), and garden cress (Lepidium sativum L.) were cultivated in hydroponic media, to which the coumarin was applied. Uptake of umbelliferone was verified by corresponding HPLC analyses of extracts obtained from the aerial parts of the seedlings. In all cases, a tremendous uptake of umbelliferone was observed. In plants that genuinely contain coumarins, the umbelliferone taken up was modified: in garden cress, it was hydroxylated and glucosylated to yield esculin, while in barley seedlings, the imported umbelliferone was modified by methoxylation to yield scopoletin. Corresponding reactions are known from modifications of xenobiotics to be catalyzed by cytochrome P450 enzymes. Accordingly, in an additional approach, umbelliferone was applied together with naproxen, which is reported to reduce enzyme activity of P450 enzymes. As predicted, the conversion of umbelliferone to scopoletin in barley as well as the modification to esculin in garden cress was strongly reduced by the addition of naproxen. These data for the first time demonstrate that – in addition to alkaloids – also phenolic compounds are taken up by various acceptor plants. Apart from the leaching of rotting plants, coumarins are known to be exuded by many plants. Accordingly, these compounds are frequently present in soils and will be taken up. These coherences imply that the horizontal natural product transfer might represent a more general phenomenon in plant ecology. Moreover, this study outlines that – in analogy to the modification of xenobiotics – also natural products taken up are modified in the acceptor plants.

Copyright ? 2018 Elsevier Ltd. All rights reserved.

KEYWORDS

Biotransformation; Coumarins; Esculin; Glucosylation; Hordeum vulgare L.; Horizontal transfer; Hydroxylation; Lepidium sativum L.; Linum usitatissimum L.; Pisum sativum L.; Raphanus sativus L.; Scopoletin; Umbelliferone

Title

Uptake and modification of umbelliferone by various seedlings.

Author

Hijazin T1, Radwan A2, Abouzeid S3, Drager G4, Selmar D5.

Publish date

2019 Jan

PMID

29188498

Abstract

The present study was to investigate cardioprotective effects of umbelliferone (Umb) on coronary artery ligation-induced myocardial ischemia. The model of myocardial ischemia (MI) was induced by ligatured the left anterior descending coronary artery of SD rats. ST-segment elevation, lactate dehydrogenase (LDH), creatine kinase (CK), catalase (SOD), malondialdehyde (MDA), inflammatory cytokines, Toll-like receptors (TLRs)/nuclear factor (NF)-κBp65 pathway, and apoptosis were evaluated in rats treated with or without Umb. The results showed that Umb treatment could significantly decrease the elevation of the ST segment of electrocardiograph (ECG), the myocardial infarct size of MI significantly. The levels of LDH, CK, and MDA were suppressed, and the content of SOD was enhanced with Umb. The elevated concentration of inflammatory cytokines such as tumor necrosis factor-alpha (TNF-α), interleukin-1 beta (IL-1β), and IL-6 in MI rats was effectively reversed by the Umb administration. Also, TLR/NF-κB and apoptosis-related proteins in MI rats were restored respectively by Umb treatment. The protective effect of Umb against MI injury might be associated with inflammation and apoptosis pathway.

KEYWORDS

apoptosis; inflammation; myocardial ischemia; umbelliferone

Title

Umbelliferone Alleviates Myocardial Ischemia: the Role of Inflammation and Apoptosis.

Author

Gan J1, Qian W1, Lin S2.

Publish date

2018 Mar

PMID

28089948

Abstract

Umbelliferone was an important allelochemical with a wide spectrum bioactivity. In our previous study, C7 hydroxy in the backbone of umbelliferone was identified to be responsible for its phytotoxicity and the targeted modification of the above site could lead to the phytotoxicity loss. In view of this, a series of hydroxycoumarins and C7 O-substituted umbelliferone derivatives were efficiently synthesized to evaluate their antifungal activity against four phytopathogenic fungi. Most of them, as we predicted, exhibited improved fungicidal activity. The phytotoxicity of effective compounds was also assayed by Lactuca sativa to investigate their side effects on plant growth. Compounds 9 and 17 were identified to show strong antifungal activity with low phytotoxicity. A brief investigation on structure-activity relationships revealed that the modification at the C7 hydroxy of umbelliferone could be a promising way to enhance the antifungal activity with decreasing the phytotoxicity.

Copyright ? 2017 Elsevier Ltd. All rights reserved.

KEYWORDS

EC(50) values; Fungicidal activity; Structure-activity relationships; Umbelliferone derivatives

Title

Antifungal activity of umbelliferone derivatives: Synthesis and structure-activity relationships.

Author

Pan L1, Li X2, Jin H3, Yang X3, Qin B4.

Publish date

2017 Mar


Description :

Umbelliferone, a natural product of the coumarin family, is a fluorescing compound which can be used as a sunscreen agent.