Bourgeonal
(Synonyms: 4-(1,1-二甲基乙基)苯丙醛) 目录号 : GC46945
An hOR17-4 agonist
Cas No.:18127-01-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Bourgeonal is an agonist of human testicular olfactory receptor hOR17-4.1 It increases cytosolic calcium levels in human spermatozoa when used at a concentration of 5 μM. Bourgeonal acts as a chemoattractant and increases swimming speed in sperm chemotaxis assays in a concentration-dependent manner.
1.Spehr, M., Gisselmann, G., Poplawski, A., et al.Identification of a testicular odorant receptor mediating human sperm chemotaxisScience299(5615)2054-2058(2003)
| Cas No. | 18127-01-0 | SDF | |
| 别名 | 4-(1,1-二甲基乙基)苯丙醛 | ||
| Canonical SMILES | CC(C)(C)C1=CC=C(CCC=O)C=C1 | ||
| 分子式 | C13H18O | 分子量 | 190.3 |
| 溶解度 | DMF: 15mg/mL,DMSO: 10mg/mL,Ethanol: 30mg/mL,Ethanol:PBS (pH 7.2) (1:3): 0.25mg/mL | 储存条件 | Store at -20°C |
| 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 | 5.2549 mL | 26.2743 mL | 52.5486 mL |
| 5 mM | 1.051 mL | 5.2549 mL | 10.5097 mL |
| 10 mM | 0.5255 mL | 2.6274 mL | 5.2549 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 | ||||||||||
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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。
Human olfactory sensitivity for Bourgeonal and male infertility: a preliminary investigation
Eur Arch Otorhinolaryngol 2013 Nov;270(12):3079-86.PMID:23525651DOI:10.1007/s00405-013-2441-0.
Olfactory receptor (OR) expression is also present in the sperm cells and could mediate sperm chemotaxis. OR1D2 was the first OR expressed in the testis demonstrated to be involved in chemotaxis and to be expressed also in the nose with a similar behavior. Bourgeonal is the OR1D2 most potent known agonist. Infertility affects ~15 % of couples in western countries and sometimes it is unexplained. This pilot study compared the Bourgeonal olfactory thresholds, the ability of sperm to sense the Bourgeonal and the frequency of 13 single nucleotide polymorphisms (SNPs) of OR1D2 gene in nine males suffering of unexplained infertility with a control group of 15 healthy males. The mean olfactory threshold for Bourgeonal was statistically different between the study group (10.5 ± 3.7; median 12.3) and the control group (14.0 ± 2.8; median 15.5) (p = 0.006). Statistical analysis showed a significantly higher percentage of spermatozoa that migrated toward the capillaries filled with Bourgeonal in the control group compared to the study group (p < 0.0001). Sperm migration was equally inhibited in both groups of subjects when, together with Bourgeonal, capillaries were filled with undecanal, a strong Bourgeonal inhibitor (p = 0.42). The 13 SNPs of OR1D2 revealed a statistically significant difference for allele and genotype frequency of rs769423 in study group versus control group (p = 0.02). The present preliminary study seems to confirm the important role of OR1D2 both in nose and spermatozoa and may explain the idiopathic infertility of the study group. Further studies on larger series are mandatory to confirm our preliminary evidence.
Olfactory threshold for Bourgeonal and sexual desire in young adult males
Med Hypotheses 2015 May;84(5):437-41.PMID:25665864DOI:10.1016/j.mehy.2015.01.035.
Olfactory receptors were found to be expressed also in human sperm giving rise to the hypothesis that they might play a role in fertility and sexual behavior. For instance, Bourgeonal was demonstrated to be an agonist of sperm cells olfactory receptor, OR1D2. OR1D2 has been found to be expressed in human olfactory epithelium and to play a critical role in human sperm chemotaxis. Recent preliminary evidence showed that olfaction sensitivity (determined by n-butanol olfactory threshold) and sexual desire were associated in young adult males. It is reasonable to hypothesize that Bourgeonal olfactory threshold could be related with human sexual behavior and desire. In 37 healthy young adult male volunteers (age range 20-36 years), the Bourgeonal odor threshold and the intensity of sexual desire [the latter using the International Index of Erectile Function (IIEF) scale] were examined. In addition, samples of DNA were collected. Allele and genotype frequency of the OR1D2 single nucleotide polymorphisms (SNPs) were then evaluated in order to study the relationship between sexual desire and OR1D2 SNPs expression. The olfactory threshold was categorized as <10, 10⩽threshold<15, 15⩽threshold<20, ⩾20. IIEF 1 and IIEF 2 scores were significantly associated. IIEF1 scores, but not IIEF2 scores were significantly associated with olfactory threshold. No statistically significant associations were found neither between genotypes frequency and sexual desire (IIEF1 and IIEF2), nor between genotypes frequency and olfactory threshold. Hypothesizing for the first time the relationship between Bourgeonal olfactory sensitivity and sexual desire in a group of young adult males, the present study found a significant association between lower olfactory threshold for Bourgeonal and stronger sexual desire, in terms of IIEF1.
Decreased perception of Bourgeonal may be linked to male idiopathic infertility
Chem Senses 2013 Jun;38(5):439-45.PMID:23535200DOI:10.1093/chemse/bjt009.
Regarding the chemotaxis of sperms, new insights have been gained during the last 20 years. Olfactory receptors are expressed on the flagellar midpiece of human spermatogenic cells. One of them, OR1D2, is also expressed in the olfactory epithelium. This receptor has been suggested to play a role in sperm chemotaxis and thus in fertility. As OR1D2 is activated by Bourgeonal, the aim of the study was to investigate whether patients with idiopathic infertility would exhibit a decreased olfactory sensitivity toward Bourgeonal. Participants were 14 patients with idiopathic infertility and 23 controls (all young fathers). After having ascertained normosmia, odor thresholds and intensity ratings for the pleasant and flowery odors of Bourgeonal, helional, and phenylethylalcohol were obtained. As a result, patients had specifically decreased intensity ratings for Bourgeonal. It suggests that men with unexplained infertility tend to be less suprathreshold sensitive toward the odor of Bourgeonal but not to that of other floral odors. It may be speculated that the decreased olfactory sensitivity relates to a decreased functionality of OR1D2, which in turn may be linked to idiopathic infertility.
Novel Bourgeonal fragrance conjugates for the detection of prostate cancer
Invest New Drugs 2013 Oct;31(5):1151-7.PMID:23508273DOI:10.1007/s10637-013-9943-x.
The methods used for detection of prostate cancer and prostate cancer lymph node metastases in medical diagnostics leave room for improvement. Currently, no means of identifying metastasized lymph nodes other than biopsies is available. Markers which are exclusively found on prostate cancer cells present a focal point for potential imaging methods. To complement the established markers like e.g. PCA3-a noncoding mRNA sequence-and PSA-a serine protease-we investigated the ectopically expressed G-protein coupled olfactory receptor OR1D2 as a possible target for prostate-specific detection with its agonist Bourgeonal which has been conjugated to two different fluorescent dyes. We performed mRNA expression analysis of the OR1D2 receptor mRNA by reverse transcriptase polymerase chain reaction on LNCaP prostate carcinoma cells and three other non-prostate derived carcinoma cell lines. Additionally, we used flow cytometry to investigate the uptake of fluorescent-dye-bound OR1D2-ligand Bourgeonal into the examined carcinoma cell lines. Finally, confocal laser scanning microscopy of in vitro cell culture and in vivo tumor xenografts on mice was performed. We could confirm OR1D2 receptor mRNA overexpression as well as stronger uptake of both Bourgeonal conjugates in vitro and in vivo for LNCaP cells compared to the non-prostate derived cell lines. Cytoplasmic accumulation and no adverse effects after in vitro and in vivo application of the conjugates were observed. The conjugates represent a platform for the development of future prostate-specific imaging applications, e.g. detection of metastasized lymph nodes during surgery by intraoperative laser examination.
Odor interaction between Bourgeonal and its antagonist undecanal
Chem Senses 2009 Sep;34(7):625-30.PMID:19620388DOI:10.1093/chemse/bjp044.
The perceived quality of a binary mixture will, as a rule of thumb, be dominated by the quality of the stronger unmixed component. On the other hand, there are mechanisms that, in theory, suggest that this will not always be true; one example being receptor antagonism. Undecanal has been indicated as an antagonist for bourgeonal-sensitive receptors in the human olfactory epithelium. Therefore, we investigated mixtures of isointense concentrations of Bourgeonal and undecanal and, as a control, mixtures of isointense concentrations of Bourgeonal and n-butanol. Both mixture types were investigated at 2 levels of concentration. The particular aim was to see if the bourgeonal-undecanal mixtures would exhibit asymmetric odor quality favoring the perception of the antagonist and the control mixture would not. For the control mixture, indeed odor quality tended to be dominated by the strongest component before mixing as would be suggested from previous studies. In line with the hypothesis, the bourgeonal-undecanal mixture was dominated by the antagonist's quality, but only when mixed at higher concentrations, altogether suggesting the effects of a low-affinity receptor antagonism. This is, to our knowledge, the first demonstration of how antagonistic interaction at the level of the receptor can affect the perception of odor mixtures in humans.