Catalogue Number
BF-H3019
Analysis Method
HPLC,NMR,MS
Specification
98%
Storage
2-8°C
Molecular Weight
162.14
Appearance
White crystalline powder
Botanical Source
Xanthoceras sorbifolium,Morus alba,Ipomoea nil,Artemisia argyi,Carthamus tinctorius
Structure Type
Phenylpropanoids
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
2932200000
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
MSDS
30439620
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.
Biotransformation; Coumarins; Esculin; Glucosylation; Hordeum vulgare L.; Horizontal transfer; Hydroxylation; Lepidium sativum L.; Linum usitatissimum L.; Pisum sativum L.; Raphanus sativus L.; Scopoletin; Umbelliferone
Uptake and modification of umbelliferone by various seedlings.
Hijazin T1, Radwan A2, Abouzeid S3, Drager G4, Selmar D5.
2019 Jan
29188498
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.
apoptosis; inflammation; myocardial ischemia; umbelliferone
Umbelliferone Alleviates Myocardial Ischemia: the Role of Inflammation and Apoptosis.
Gan J1, Qian W1, Lin S2.
2018 Mar
28089948
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.
EC(50) values; Fungicidal activity; Structure-activity relationships; Umbelliferone derivatives
Antifungal activity of umbelliferone derivatives: Synthesis and structure-activity relationships.
Pan L1, Li X2, Jin H3, Yang X3, Qin B4.
2017 Mar
