Didymic acid
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| Category | Others |
| Catalog number | BBF-05391 |
| CAS | 436-74-8 |
| Molecular Weight | 370.44 |
| Molecular Formula | C22H26O5 |
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Specification
| Synonyms | 3-hydroxy-7-methoxy-1-pentyl-9-propyldibenzo[b,d]furan-2-carboxylic acid; 3-hydroxy-7-methoxy-1-pentyl-9-propyl-2-dibenzofurancarboxylic acid; Incrassatic acid; Didymsaeure |
| IUPAC Name | 3-hydroxy-7-methoxy-1-pentyl-9-propyldibenzofuran-2-carboxylic acid |
| Canonical SMILES | CCCCCC1=C(C(=CC2=C1C3=C(C=C(C=C3O2)OC)CCC)O)C(=O)O |
| InChI | InChI=1S/C22H26O5/c1-4-6-7-9-15-20(22(24)25)16(23)12-18-21(15)19-13(8-5-2)10-14(26-3)11-17(19)27-18/h10-12,23H,4-9H2,1-3H3,(H,24,25) |
| InChI Key | IDZVZCQOFFSQMO-UHFFFAOYSA-N |
Properties
| Boiling Point | 449.0±14.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Production and Activity of Cristazarin in the Lichen-Forming Fungus Cladonia metacorallifera
Min-Hye Jeong, Chan-Ho Park, Jung A Kim, Eu Ddeum Choi, Soonok Kim, Jae-Seoun Hur, Sook-Young Park J Fungi (Basel). 2021 Jul 26;7(8):601. doi: 10.3390/jof7080601.
Lichens are a natural source of bioactive compounds. Cladonia metacorallifera var. reagens KoLRI002260 is a rare lichen known to produce phenolic compounds, such as rhodocladonic, thamnolic, and didymic acids. However, these metabolites have not been detected in isolated mycobionts. We investigated the effects of six carbon sources on metabolite biosynthesis in the C. metacorallifera mycobiont. Red pigments appeared only in Lilly and Barnett's media with fructose at 15 °C after 3 weeks of culture and decreased after 6 weeks. We purified these red pigments using preparative-scale high performance liquid chromatography and analyzed them via nuclear magnetic resonance. Results indicated that 1% fructose-induced cristazarin and 6-methylcristazarin production under light conditions. In total, 27 out of 30 putative polyketide synthase genes were differentially expressed after 3 weeks of culture, implying that these genes may be required for cristazarin production in C. metacorallifera. Moreover, the white collar genes Cmwc-1 and Cmwc-2 were highly upregulated at all times under light conditions, indicating a possible correlation between cristazarin production and gene expression. The cancer cell lines AGS, CT26, and B16F1 were sensitive to cristazarin, with IC50 values of 18.2, 26.1, and 30.9 μg/mL, respectively, which highlights the value of cristazarin. Overall, our results suggest that 1% fructose under light conditions is required for cristazarin production by C. metacorallifera mycobionts, and cristazarin could be a good bioactive compound.
2. Dibenzofurans from Lichens - A Pharmacological Overview
Isabel Ureña-Vacas, Elena González Burgos, Pradeep Kumar Divakar, Maria Pilar Gómez-Serranillos Curr Top Med Chem. 2021;21(26):2397-2408. doi: 10.2174/1568026621666210728095214.
Lichens are a symbiotic association between a fungus (mycobiont) and a green algae/- cyanobacterium (photobiont). Lichens are a source of secondary metabolites, most of them being exclusively for these species, among which dibenzofurans are found. Dibenzofurans are a small group (over 35 different identified compounds), being usnic acid the most studied. In the last 10 years, there has been a growing interest in the pharmacological activity of dibenzofurans. In this work, dibenzofurans isolated from lichens (alectosarmentin, condidymic acid, didymic acid, isousnic acid, isostrepsilic acid, usimines A-C and usnic acid) were reviewed, most of which showed antibacterial, antifungal, and cytotoxic activities. These findings provide future guidance for research on pharmacological activity of dibenzofurans.
3. Uncommon chlorinated xanthone and other antibacterial compounds from the lichen Cladonia incrassata
Amandine Dieu, Marion Millot, Yves Champavier, Lengo Mambu, Vincent Chaleix, Vincent Sol, Vincent Gloaguen Planta Med. 2014 Jul;80(11):931-5. doi: 10.1055/s-0034-1382827. Epub 2014 Jul 16.
Bioassay-guided fractionation of an extract of the lichen Cladonia incrassata against Staphylococcus aureus led to a novel compound, 1,5-dihydroxy-2,4,6-trichloro-7-methylxanthone (1), along with six known compounds: (-)-usnic acid (2), didymic acid (3), condidymic acid (4), squamatic acid (5), thamnolic acid (6), and prasinic acid (7). Didymic, condidymic, and prasinic acids were isolated for the first time from C. incrassata. Didymic, condidymic, and (-)-usnic acids were active against S. aureus (a minimum inhibitory concentration of 7.5 µg/mL).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
