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Monographs of fragrance chemicals and extracts that have caused contact allergy / allergic contact dermatitis
Published in Anton C. de Groot, Monographs in Contact Allergy, 2021
In two commercial treemoss absolutes, the presence of a mixture of resin acids accounting for 11.4% (wt./wt.) and 8.1% (wt./wt.) of the material, respectively, was identified. The major compound was dehydroabietic acid, together with abietic acid and its isomers. Also, the samples proved to contain 1.6% resp. 1.1% of 7-oxo-dehydroabietic acid, an important sensitizer in colophonium (24). To investigate whether patients allergic to colophonium would also react to treemoss, these 2 samples (1% and 2% pet.) were patch tested in 17 patients known to be allergic to colophonium. Twelve patients (71%) reacted to the treemoss samples. It was concluded that treemoss absolute contains enough resin acids and oxidation products to elicit a positive reaction in the great majority of colophonium-allergic patients (24).
Catalog of Herbs
Published in James A. Duke, Handbook of Medicinal Herbs, 2018
Dragon’s blood consists of 56% resin alcohol dracoresinotannol — associated with benzoic and benzoylacetic acids; also, benzoyl acetic ester, dracorsene, dracoalban, and cinnamic acid.12,16 Abietic acid has been isolated from the resin acids. The principal pigment is dracocarmin, C31H26O5, an anthocyanadin, with another dracorubin, C28H24O7, also reported.1
Terpenes and Terpenoids
Published in William J. Rea, Kalpana D. Patel, Reversibility of Chronic Disease and Hypersensitivity, Volume 4, 2017
William J. Rea, Kalpana D. Patel
Diterpenes emanate from the resins of various coniferous species. Abietic acid derivatives are the principal product of rosin, a resin that comes mainly from pine and has a variety of industrial uses, most of which exacerbate sensitivity in the individual who is chemically sensitive. Labdanes and clerodanes are the “bitter” principle of bark, roots, and stems (from clerodane and horehound).78
Combining a bio-based polymer and a natural antifoulant into an eco-friendly antifouling coating
Published in Biofouling, 2020
Ho Yin Chiang, Jiansen Pan, Chunfeng Ma, Pei-Yuan Qian
Poly(L-lactide) diol (PLA, Mw = 2,000g mol−1) from Daigang Biomaterial (Jinan, China) and 1,4-butanediol (BDO) from Shanghai Aladdin Bio-Chem Technology Co., Ltd (Shanghai, China) were dried at 110°C under reduced pressure for 2h prior to use. Isophorone diisocyanate (IPDI) and dibutyltin dilaurate (DBTDL) from Shanghai Aladdin Bio-Chem Technology Co., Ltd (Shanghai, China) were used as received. Tetrahydrofuran (THF) from Innochem (Beijing) Technology Co., Ltd (Beijing, China) was refluxed over CaH2 and distilled prior to use. Rosin, a naturally occurring resin that mainly consists of abietic acid (C19H29COOH), was obtained from Wuzhou Sun Shine Forestry & Chemicals Co., Ltd (Guangxi, China). Synthesized 5-octylfuran-2(5H)-one (butenolide) with a purity exceeding 99% was purchased from ChemPartner Co., Ltd (Shanghai, China) and used as received. Artificial seawater (ASW) was prepared according to ASTM D1141-98 (2013b). Epoxy panels and polyvinyl chloride (PVC) panels were obtained from local hardware stores in Hong Kong.
Design and synthesis of tricyclic terpenoid derivatives as novel PTP1B inhibitors with improved pharmacological property and in vivo antihyperglycaemic efficacy
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2020
Lingling Yang, Feng Chen, Cheng Gao, Jiabao Chen, Junyan Li, Siyan Liu, Yuanyuan Zhang, Zhouyu Wang, Shan Qian
The synthesis procedure to achieve 15-hydroxydehydroabietic acid (3) from abietic acid (AA) involved addition, elimination, and oxidation. However, according to the literatures36–38, alcohol 3 was obtained in only 10% yield in our laboratory. We therefore improved the synthetic method and 3 was finally obtained in 70% overall yield (Scheme 1). According to the improved synthetic procedure, AA (1) was treated with 33% HBr/AcOH and the resulting 8, 15-dibromo derivative was heated in the presence of LiOH/DMF to afford diene (2), with four methyl groups of all singlets by 1HNMR. Oxidative rearrangement of 2 with SeO2 provided 15-hydroxydehydroabietate (3) in 80% yield. 3 was esterified by treatment with EtI (or BnBr) to give ester 4a (4 b). 4a was then reduced with LiAlH4 to give alcohol 5. We found 15-hydroxydehydroabietic derivatives are not suitable synthesis intermediates because of high steric hindrance of C-15 position, and thus hydroperoxide rearrangement of esters 4a–b with t-BuOOH and H2SO4/AcOH gave the 13-hydroxy-8,11,13-podocarpatriene derivatives (6a–b)39. Finally, ester 6a was saponified with aq.NaOH to give acid 7.
Quantitative structure–activity relationship models for compounds with anticonvulsant activity
Published in Expert Opinion on Drug Discovery, 2019
Carolina L. Bellera, Alan Talevi
The discriminant function was initially used to screen Merck Index database, discovering the anticonvulsants effects of abietic acid [76], preservatives methyl and propylparaben [51] and the artificial sweeteners acesulfame and sodium cyclamate [77]. Particular attention was given to food and medication additives since it was argued that they present well-characterized short- and long-term toxicity profiles. Regarding artificial sweeteners with anticonvulsant effects, it was hypothesized based on bioinformatic analysis that they might be targeting metabotropic glutamate receptors in the brain [75], although such hypothesis was not challenged experimentally. A subsequent article from the same group proved that sodium cyclamate is an nM inhibitor of carbonic anhydrase isoform VII, which has been proposed as an AED target [78].