Damascenone
(Synonyms: 大马酮,(E/Z)-Damascenone) 目录号 : GC62674
Damascenone is a potent flavor compound, possessing an extremely low odor threshold of 0.002 ppb in water.
Cas No.:23696-85-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Damascenone is a potent flavor compound, possessing an extremely low odor threshold of 0.002 ppb in water.
| Cas No. | 23696-85-7 | SDF | |
| 别名 | 大马酮,(E/Z)-Damascenone | ||
| 分子式 | C13H18O | 分子量 | 190.28 |
| 溶解度 | DMSO : 100 mg/mL (525.54 mM; Need ultrasonic) | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.2554 mL | 26.2771 mL | 52.5541 mL |
| 5 mM | 1.0511 mL | 5.2554 mL | 10.5108 mL |
| 10 mM | 0.5255 mL | 2.6277 mL | 5.2554 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Occurrence, sensory impact, formation, and fate of Damascenone in grapes, wines, and other foods and beverages
J Agric Food Chem 2011 Sep 28;59(18):9717-46.PMID:21866982DOI:10.1021/jf201450q.
Among plant-derived odorants, Damascenone is one of the most ubiquitous, sometimes occurring as an apparent natural product but more commonly occurring in processed foodstuffs and beverages. It has been widely reported as a component of alcoholic beverages, particularly of wines made from the grape Vitis vinifera . Although Damascenone has one of the lowest ortho- and retronasal detection thresholds of any odorant, its contribution to the sensory properties of most products remains poorly understood. Damascenone can be formed by acid-catalyzed hydrolyses of plant-derived apocarotenoids, in both aglycon and glycoconjugated forms. These reactions can account for the formation of Damascenone in some, but not all, products. In wine, Damascenone can also be subject to degradation processes, particularly by reaction with sulfur dioxide.
Fragrance material review on Damascenone
Food Chem Toxicol 2007;45 Suppl 1:S172-8.PMID:18031890DOI:10.1016/j.fct.2007.09.056.
A toxicologic and dermatologic review of Damascenone when used as a fragrance ingredient is presented.
Formation of Damascenone under both commercial and model fermentation conditions
J Agric Food Chem 2011 Feb 23;59(4):1338-43.PMID:21254776DOI:10.1021/jf103741n.
The fermentations, at a commercial winery, of six different grape musts encompassing the varieties Riesling, Chardonnay, Sauvignon blanc, Shiraz, Grenache, and Pinot noir were monitored for Damascenone concentration. In every case, the concentration of Damascenone increased during fermentation from low or undetectable levels to concentrations of several parts per billion. Further increases in Damascenone concentration were observed during barrel aging of three of these wines. Two ketones, megastigma-4,6,7-triene-3,9-dione (4) and 3-hydroxymegastigma-4,6,7-trien-9-one (5), were synthesized and subjected to fermentation conditions using two yeasts, AWRI 796, and AWRI 1537. In the case of the former compound, 4, synthesis confirmed the original, tentative assignment of the structure and confirmed 4 as a natural product, isolated from honey. Both compounds, under the action of both yeasts, produced appreciable amounts of Damascenone (1), with ketone 5 and AWRI 796 yeast yielding the highest concentration of 1.
Rationalizing the formation of Damascenone: synthesis and hydrolysis of Damascenone precursors and their analogues, in both aglycone and glycoconjugate forms
J Agric Food Chem 2008 Oct 8;56(19):9183-9.PMID:18767865DOI:10.1021/jf8018134.
Storage of megastigma-4,6,7-trien-3,9-diol (5), and megastigma-3,4-dien-7-yn-9-ol (6) in aqueous ethanol solution at pH 3.0 and 3.2 gave exclusively Damascenone (1) and Damascenone adducts at room temperature. The diol (5) had half-lives for the conversion of 32 and 48 h at pH 3.0 and pH 3.2, respectively. The acetylenic alcohol (6) had half-lives of 40 and 65 h at the same pH levels. In order to study the reactivity of the C-9 hydroxyl function in 5 and in the previously investigated allenic triol 2, two model compounds, megastigma-4,6,7-trien-9-ol (7) and megastigma-6,7-dien-9-ol (8) were synthesized. No 1,3-transposition of oxygen to form analogues of Damascenone was observed when 7 and 8 were subjected to mild acidic conditions. Such transposition takes place only with highly conjugated acetylenic precursors such as 6 or tertiary allenic alcohols such as 2. The placement of glucose at C-3 of 5 and at C-9 of 6 gave the glycosides 9 and 10, respectively. The effect of such glucoconjugation was to increase the observed half-lives by a factor of only 1.6-1.7 for the allenic glucoside 9, and by 2.1-2.2 for the acetylenic glucoside 10. These studies indicate that the effect of glycosylation on Damascenone formation is probably not important on the time scale of wine making and maturation.
Fate of Damascenone in wine: the role of SO2
J Agric Food Chem 2004 Dec 29;52(26):8127-31.PMID:15612806DOI:10.1021/jf048582h.
Damascenone has been shown to undergo reaction with common wine components. Following the action of acid and heat alone, two bicyclic compounds, 4,9,9-trimethyl-8-methylenebicyclo[3.3.1]non-6-en-2-one (2) and 4,4,9-trimethyl-8-methylenebicyclo[3.3.1] non-6-en-2-one (3), were isolated. However, this conversion takes place only very slowly, if at all, under milder conditions (45 degrees C). When treated with a variety of nucleophiles at pH 3.0 and 5.5, the concentration of Damascenone in buffered aqueous ethanol decreased by minor amounts (10-20%) except for cysteine and 2-mercaptoethanol addition at pH 5.5 (approximately 40 and approximately 30%, respectively) and SO2 (>90% at pH 3.0; 100% at pH 5.5). An adduct from this last combination was prepared and shown to be the C9 sulfonic acid derivative of Damascenone. A detailed investigation into the effect of SO2 demonstrated that loss of Damascenone in model wine was directly related to the concentration of added SO2 but was essentially unaffected by small changes in pH.