CAS: 116-26-7; 2,6,6-Trimethylcyclohexa-1,3-Dienecarbaldehyde

化学文摘社编号116-26-7是一个独特的识别标志,便于在化学数据库中识别这种化合物.总的来说,萨法兰不仅因其感官特性,而且因其潜在的健康利益而具有价值,因此它不仅在食品和制药业中都具有利益.

结构式图片

相似化合物

23696-85-7 3383-21-9 35044-59-8

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

1-hydroxymethyl-2,6,6-trimethylcyclohexa-1,3-diene 2,6,6-trimethylcyclohexa-1,3-dienecarbonitrile safranal 2,6,6-trimethylcyclohex-1-enecarbaldehyde2,6,6-trimethyl-cyclohexa-1,3-dienecarbaldehyde-oxime 2,6,6-trimethyl-cyclohexa-1,3-dienecarbaldehyde-thiosemicarbazone 2,6,6-trimethyl-cyclohexa-1,3-dienecarbaldehyde-(2,4-dinitro-phenylhydrazone) (E)-1,1,1-Trifluoro-4-(2,6,6-trimethyl-cyclohexa-1,3-dienyl)-but-3-en-2-one

合成工艺路线路线简述

  • 合成目标产物 Safranal 主要起始原料 Geranyl Acetate
  • (文献来源)合成步骤主要原料 Geranyl Acetate
📜1-Hydroxy-2,2,6-Trimethyl-Cyclohexanecarbonitrile置于吡啶,Sodium Tetrahydroborate,N-溴代丁二酰亚胺(Nbs),氯化亚砜,Cerium(III) Chloride,二异丁基氢化铝,对甲苯磺酸,Calcium Carbonate,过氧化苯甲酰体系中,用 甲醇,四氯化碳,水,甲苯,苯 用作溶剂,化学反应 60.25H,反应生成2,3-二氢-2,2,6-三甲基苯甲醛
参考文献:Kutney,James P.; Gunning,Philip J.; Clewley,Robin G.,Canadian Journal Of Chemistry,1992,Vol. 70,# 7,P. 2094-2114
标题:Kutney,James P.; Gunning,Philip J.; Clewley,Robin G.,Canadian Journal Of Chemistry,1992,Vol. 70,# 7,P. 2094-2114

海关参考信息

专利信息


专利号:US-8222458-B2
优先权日:2008-06-13
标题 :Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin
发明人:KHACHIK FREDERICK; CHANG AN-NI
权利人:KHACHIK FREDERICK; CHANG AN-NI; UNIV MARYLAND
摘要:Disclosed is a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydrox-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)-C 15 -Wittig salt] and its (3S)-enantiomer [(3S)-C 15 -Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercial available 2,5- dimethtylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin. Similarly, (3R)-C 15 -Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal.

专利号:WO-2020158831-A1
优先权日:2019-01-30
标 题:Transdermal absorption composition with controlled release of water-soluble hydrochloride
发明人:ONO FUMIYASU; GOTO MASAHIRO
权利人:UNIV KYUSHU NAT UNIV CORP; NISSAN CHEMICAL CORP
摘要:The objective of the present invention is to provide a method for simply raising the transdermal absorption properties of a water-soluble hydrochloride without forming a prodrug by organic synthesis. The present invention relates to: a composition containing a water-soluble hydrochloride and a liposoluble compound having an aldehyde group; a transdermal absorption composition containing said composition, a transdermal absorption control agent, and a liposoluble medium; and a method for controlling the release of the water-soluble hydrochloride from the composition into the skin.

专利号:US-2009311761-A1
优先权日:2008-06-13
标题 :Process for Synthesis of (3S)- and (3R)-3-Hydroxy-Beta-Ionone, and Their Transformation to Zeaxanthin and Beta-Cryptoxanthin

专利号:WO-2016016789-A1
优先权日:2014-07-29
标 题:Aromatic compositions and methods for their production
发明人:EYAL AHARON
权利人:EYAL RES CONSULTANTS LTD
摘要:Disclosed are aroma compositions comprising a key plant aroma compound, plant aroma co-extracts and a synthesis co-product. Also disclosed are methods for the production of such aroma composition and products comprising them.

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献


1: Lertnimitphun P, Zhang W, Fu W, Yang B, Zheng C, Yuan M, Zhou H, Zhang X, Pei W, Lu Y, Xu H. Safranal Alleviated OVA-Induced Asthma Model and Inhibits Mast Cell Activation. Front Immunol. 2021 May 20;12:585595. doi: 10.3389/fimmu.2021.585595.
2: Esmaealzadeh D, Moodi Ghalibaf A, Shariati Rad M, Rezaee R, Razavi BM, Hosseinzadeh H. Pharmacological effects of Safranal: An updated review. Iran J Basic Med Sci. 2023;26(10):1131-1143. doi: 10.22038/IJBMS.2023.69824.15197.
3: Fazeli E, Ghalibaf MHE, Forouzanfar F. Neuroprotective Potency of Safranal Against Neurological Disorders. Curr Mol Med. 2023;23(9):952-959. doi: 10.2174/1566524023666221117104612.

合成参考文献


参考文献:10.3109/13880209.2011.558103
摘要:Hooshmandi Z, Rohani AH, Eidi A, Fatahi Z, Golmanesh L, Sahraei H. Reduction of metabolic and behavioral signs of acute stress in male Wistar rats by saffron water extract and its constituent safranal. Pharm Biol. 2011 Sep;49(9):947–54. doi: 10.3109/13880209.2011.558103.
参考文献:10.14715/cmb/ 2016.62.14.2|10.14715/cmb/2016.62.14.2
摘要:Pan PK, Qiao LY, Wen XN. Safranal prevents rotenone-induced oxidative stress and apoptosis in an in vitro model of Parkinson's disease through regulating Keap1/Nrf2 signaling pathway. Cell Mol Biol (Noisy-le-grand). 2016 Dec 30;62(14):11–7. doi: 10.14715/cmb/ 2016.62.14.2.
参考文献:10.1016/j.foodchem.2020.127786
摘要:Moratalla-López N, Parizad S, Habibi MK, Winter S, Kalantari S, Bera S, Lorenzo C, García-Rodríguez MV, Dizadji A, Alonso GL. Impact of two different dehydration methods on saffron quality, concerning the prevalence of Saffron latent virus (SaLV) in Iran. Food Chem. 2021 Feb 01;337():127786. doi: 10.1016/j.foodchem.2020.127786.
参考文献:10.1021/jf0612326
摘要:Carmona M, Zalacain A, Salinas MR, Alonso GL. Generation of saffron volatiles by thermal carotenoid degradation. J Agric Food Chem. 2006 Sep 06;54(18):6825–34. doi: 10.1021/jf0612326.
参考文献:10.1002/ptr.1749
摘要:Assimopoulou AN, Sinakos Z, Papageorgiou VP. Radical scavenging activity of Crocus sativus L. extract and its bioactive constituents. Phytother Res. 2005 Nov;19(11):997–1000. doi: 10.1002/ptr.1749.
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