Incubation of alpha-cedrol and caryophyllene oxide with Neurospora crassa /identified/ 12beta-hydroxy cedrol, 10alpha-hydroxycedrol, and 3beta-hydroxy cedrol, and 12beta-hydroxy caryophyllene oxide as major metabolites, respectively. The antibacterial and radical scavenging activities of the metabolites were evaluated in vitro using broth microdilution and bioauthographic techniques. However, no significant antibacterial and antioxidant activities were observed ...
Microbial transformation of (+)-cedrol was investigated by using Staphylococcus epidermidis and found that stereospecific hydroxylation of (+)-cedrol occurred at the C-3 position to form (+)-(3S)-3-hydroxycedrol.
IDENTIFICATION AND USE: Cedrol forms colorless crystals. It is found in the wood of cypresses and cedars such as Cedrus atlantica, Cupressus sempervirens, and Juniperus virginiana. It is used in fragnances and as a flavor ingredient in foods and traditional medicine. HUMAN EXPOSURE AND TOXICITY: In an exposure study, odorized and blank air was presented to 26 healthy adult volunteers. A constant concentration of cedrol was presented for 10 minutes with 8 minute blank air intervals. Cedrol caused a relaxant effect with decreased heart rate, respiratory rate, systolic and diastolic blood pressure and increased baroreflex activity. Parasympathetic activity was increased and sympathetic activity was decreased. In another exposure study, a maximization test was carried out with 8% cedrol in petrolatum on 25 male volunteers. Sensitization reactions were observed in 2/25 volunteers. In a pre-test for a human maximization study, no irritation was observed to 8% cedrol, when applied for 48 hr under occlusion on five volunteers. In another study, Pyrolae herba (PHVO) was evaluated for antiproliferative activity against human chondrosarcoma cells. A total of 12 components in PHVO were identified. The major compounds included cedrol (17.08%). PHVO demonstrated potent antitumor activity against SW1353 cells, suggesting its potential use as a therapeutic agent in the treatment of chondrosarcoma. In another study, the aim was to investigate the inhibitory effects of cedrol on the activities of eight major human cytochrome P-450 (CYP) enzymes to assess potential cedrol drug interactions. Cedrol, was found to be a potent competitive inhibitor of CYP2B6-mediated bupropion hydroxylase with inhibition constant (Ki) values of 0.9 uM, comparable with that of a selective CYP2B6 inhibitor, thioTEPA (Ki, 2.9 uM). Cedrol also markedly inhibited CYP3A4-mediated midazolam hydroxylation with a Ki value of 3.4 uM, whereas beta-cedrene moderately blocked CYP3A4. Cedrol at 100 microM negligibly inhibited CYP1A2, CYP2A6, and CYP2D6 activities. Cedrol weakly inhibited CYP2C8, CYP2C9, and CYP2C19 activities, but beta-cedrene did not. These in vitro results indicate that cedrol should be examined for potential pharmacokinetic drug interactions in vivo due to their potent inhibition of CYP2B6 and CYP3A4. ANIMAL STUDIES: A 28-day oral toxicity study was conducted to evaluate toxicity of cedrol in rats. Sixty rats were randomly divided into five groups (10 males or 10 females per group) and a control group of 10 animals. Approximately 0.169% w/v of cedrol was administered at dose of 8.4 mg/kg/day in 20 rats (10/sex) seven days per week via gavage to all the animals for 30 days. Crooked incisors and a swollen mouth were observed in one male rat on day 28. Decrease in absolute brain weight and brain-and ovary-to body weight was observed in female rats. However, these findings were not consistent between the sexes and absence of correlative clinical changes made the consideration of these non-adverse findings of limited toxicological significance. Open epicutaneous tests were carried out in outbred male and female guinea pigs with 8% cedrol, no sensitization reactions were observed. In another study on the sedative effects of cedrol, rats and mice were exposed at 1.0 liter/ minute for 30 minutes. Cumulative spontaneous motor activity was found to be significantly decreased in the cedrol exposed group.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Higher alcohols (>3 carbons) and related compounds/
/SRP:/ Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Higher alcohols (>3 carbons) and related compounds/
/SRP:/ Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques, with a bag-valve-mask device, may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/
/HUMAN EXPOSURE STUDIES/ Odorized and blank air was presented to 26 healthy adult volunteers using an olfactometer with separate teflon-coated tubing and face mask systems to prevent deposition of cedrol particles. A constant concentration of 14.20 +/- 1.7 ug/L; 64 +/- 7.7x10-9 cedrol was presented for 10 minutes with 8 minute blank air intervals. Measurements of the subjects' ECGs, heart rate (HR), systolic (SBP) and diastolic (DBP) blood pressure and respiratory rate (RR) were recorded. Statistical differences between control air and odorized air were based on the paired t-test. Cedrol caused a relaxant effect with decreased heart rate, respiratory rate, systolic and diastolic blood pressure and increased baroreflex activity. Parasympathetic activity was increased and sympathetic activity was decreased.
farnesyl pyrophosphate 在
cedrol synthase gene from the transcriptome of the glandular trichomes of a woody Lamiaceae plant Leucosceptrum canum 作用下，
以
aq. buffer 为溶剂，
反应 3.0h，
生成 柏木脑
Synthesis of enantiopure C1 symmetric diphosphines and phosphino-phosphonites with ortho-phenylene backbones
摘要：
Reaction of 2-(diphenylphosphino)phenylphosphonous acid tetramethyldiamide 1 with (+)-menthol, (1S,2S,3S,5R)-isopinocampheol and (1R,2R)-trans-cyclohexanediol affords enantiopure phosphino-phosphonite ligands 3-5. The X-ray structures of 1 (space group P2(1)/n) and 3 (space group P2(f)) have been determined. The reaction of 1 with (1R,2R,3S,5R)-(-)-pinanediol proceeds diastereoselectivity to afford a novel type of enantiopure phosphino-phosphonite ligand 6 with an asymmetric substituted P atom. On reaction of (+)-cedryl alcohol with 1 the adduct 7 of the phosphonous acid 2-Ph2P-C6H4P(-O)(H)OH 9 and its dimethylammonium salt is formed through elimination of water and subsequent hydrolysis. The structure of 7 (space group P (1) over bar) was elucidated by X-ray structural analysis. Reduction of the chlorophosphine 8 with LiAlH4 yields the novel primary-tertiary phosphine 10, which is a valuable starting material for the synthesis of the enantiopure C-1 symmetric bidentate phospholane ligands 11 and 12. (C) 2001 Elsevier Science Ltd, All rights reserved.
<i>N</i>-Ammonium Ylide Mediators for Electrochemical C–H Oxidation
作者：Masato Saito、Yu Kawamata、Michael Meanwell、Rafael Navratil、Debora Chiodi、Ethan Carlson、Pengfei Hu、Longrui Chen、Sagar Udyavara、Cian Kingston、Mayank Tanwar、Sameer Tyagi、Bruce P. McKillican、Moses G. Gichinga、Michael A. Schmidt、Martin D. Eastgate、Massimiliano Lamberto、Chi He、Tianhua Tang、Christian A. Malapit、Matthew S. Sigman、Shelley D. Minteer、Matthew Neurock、Phil S. Baran
DOI：10.1021/jacs.1c03780
日期：2021.5.26
taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous buildingblocks and trivial synthesis techniques. The ylide-based approach to C–H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors
3. leads to amide products which can be hydrolyzed under mild conditions. The amidation reaction is mild, general and compatible with both primary C−H bonds of tertiary and secondary alcohols, as well as secondary C−H bonds of cyclic secondary alcohols. This method provides an easy access to free 1,2-aminoalcohols after efficient and mild cleavage of the oxime directing group and activated amide.
[EN] CLEAVABLE MULTI-ALCOHOL-BASED MICROCAPSULES<br/>[FR] MICROCAPSULES CLIVABLES À BASE D'ALCOOLS MULTIPLES
申请人：FIRMENICH & CIE
公开号：WO2021023645A1
公开（公告）日：2021-02-11
The present invention relates to a new process for the preparation of microcapsules based on cleavable multi-alcohols. Cleavable multi-alcohol-based microcapsules are also an object of the invention. Perfuming compositions and consumer products comprising said capsules, in particular perfumed consumer products in the form of home care or personal care products, are also part of the invention.
Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C–H and C–C bonds was accessible to the one-pot substitution reaction.
Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor®
作者：María González-Esguevillas、Javier Miró、Jenna L. Jeffrey、David W.C. MacMillan
DOI：10.1016/j.tet.2019.05.043
日期：2019.8
Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.
