Bourgeonal | CAS# 18127-01-0 | hOR17-4 agonist

Bourgeonal
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 574319

CAS#: 18127-01-0

Description: Bourgeonal is an agonist of human testicular olfactory receptor hOR17-4. It increases cytosolic calcium levels in human spermatozoa, acts as a chemoattractant, and increases swimming speed in sperm chemotaxis assays in a concentration-dependent manner.

Chemical Structure

Bourgeonal

CAS# 18127-01-0

Instruction

Theoretical Analysis

MedKoo Cat#: 574319
Name: Bourgeonal
CAS#: 18127-01-0
Chemical Formula: C13H18O
Exact Mass: 190.14
Molecular Weight: 190.290
Elemental Analysis: C, 82.06; H, 9.54; O, 8.41

Price and Availability

Size	Price	Availability
10mg	USD 265	2 Weeks
25mg	USD 460	2 Weeks
50mg	USD 770	2 Weeks
100mg	USD 1195	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Bourgeonal

IUPAC/Chemical Name: 4-(1,1-dimethylethyl)-benzenepropanal

InChi Key: FZJUFJKVIYFBSY-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H18O/c1-13(2,3)12-8-6-11(7-9-12)5-4-10-14/h6-10H,4-5H2,1-3H3

SMILES Code: CC(C)(C)C1=CC=C(CCC=O)C=C1

Appearance: An oil

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

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Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 190.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Sturzu A, Sheikh S, Echner H, Nägele T, Deeg M, Schwentner C, Horger M, Ernemann U, Heckl S. Novel bourgeonal fragrance conjugates for the detection of prostate cancer. Invest New Drugs. 2013 Oct;31(5):1151-7. doi: 10.1007/s10637-013-9943-x. Epub 2013 Mar 19. PMID: 23508273.

2: Ottaviano G, Zuccarello D, Menegazzo M, Perilli L, Marioni G, Frigo AC, Staffieri A, Foresta C. Human olfactory sensitivity for bourgeonal and male infertility: a preliminary investigation. Eur Arch Otorhinolaryngol. 2013 Nov;270(12):3079-86. doi: 10.1007/s00405-013-2441-0. Epub 2013 Mar 24. PMID: 23525651.

3: Sinding C, Kemper E, Spornraft-Ragaller P, Hummel T. Decreased perception of bourgeonal may be linked to male idiopathic infertility. Chem Senses. 2013 Jun;38(5):439-45. doi: 10.1093/chemse/bjt009. Epub 2013 Mar 27. PMID: 23535200.

4: Brodin M, Laska M, Olsson MJ. Odor interaction between Bourgeonal and its antagonist undecanal. Chem Senses. 2009 Sep;34(7):625-30. doi: 10.1093/chemse/bjp044. Epub 2009 Jul 20. PMID: 19620388.

5: Ottaviano G, Marioni G, Frasson G, Zuccarello D, Marchese-Ragona R, Staffieri C, Nardello E, Frigo AC, Foresta C, Staffieri A. Olfactory threshold for bourgeonal and sexual desire in young adult males. Med Hypotheses. 2015 May;84(5):437-41. doi: 10.1016/j.mehy.2015.01.035. Epub 2015 Jan 30. PMID: 25665864.

6: Wolf S, Gelis L, Dörrich S, Hatt H, Kraft P. Evidence for a shape-based recognition of odorants in vivo in the human nose from an analysis of the molecular mechanism of lily-of-the-valley odorants detection in the Lilial and Bourgeonal family using the C/Si/Ge/Sn switch strategy. PLoS One. 2017 Aug 1;12(8):e0182147. doi: 10.1371/journal.pone.0182147. PMID: 28763484; PMCID: PMC5538716.

7: Olsson P, Laska M. Human male superiority in olfactory sensitivity to the sperm attractant odorant bourgeonal. Chem Senses. 2010 Jun;35(5):427-32. doi: 10.1093/chemse/bjq030. Epub 2010 Apr 8. PMID: 20378596.

8: Larsson L, Laska M. Ultra-high olfactory sensitivity for the human sperm- attractant aromatic aldehyde bourgeonal in CD-1 mice. Neurosci Res. 2011 Dec;71(4):355-60. doi: 10.1016/j.neures.2011.08.009. Epub 2011 Aug 30. PMID: 21893110.

9: Doszczak L, Kraft P, Weber HP, Bertermann R, Triller A, Hatt H, Tacke R. Prediction of perception: probing the hOR17-4 olfactory receptor model with silicon analogues of bourgeonal and lilial. Angew Chem Int Ed Engl. 2007;46(18):3367-71. doi: 10.1002/anie.200605002. PMID: 17397127.

10: Kjeldmand L, Salazar LT, Laska M. Olfactory sensitivity for sperm-attractant aromatic aldehydes: a comparative study in human subjects and spider monkeys. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2011 Jan;197(1):15-23. doi: 10.1007/s00359-010-0580-y. Epub 2010 Sep 7. PMID: 20820786.

11: Spehr M, Gisselmann G, Poplawski A, Riffell JA, Wetzel CH, Zimmer RK, Hatt H. Identification of a testicular odorant receptor mediating human sperm chemotaxis. Science. 2003 Mar 28;299(5615):2054-8. doi: 10.1126/science.1080376. PMID: 12663925.

12: Spehr M, Schwane K, Riffell JA, Barbour J, Zimmer RK, Neuhaus EM, Hatt H. Particulate adenylate cyclase plays a key role in human sperm olfactory receptor-mediated chemotaxis. J Biol Chem. 2004 Sep 17;279(38):40194-203. doi: 10.1074/jbc.M403913200. Epub 2004 Jul 22. PMID: 15271985.

13: Hassan SS, Choudhury PP, Pal A, Brahmachary RL, Goswami A. Designing exons for human olfactory receptor gene subfamilies using a mathematical paradigm. J Biosci. 2010 Sep;35(3):389-93. doi: 10.1007/s12038-010-0044-0. PMID: 20826948.

14: Vosshall LB. Olfaction: attracting both sperm and the nose. Curr Biol. 2004 Nov 9;14(21):R918-20. doi: 10.1016/j.cub.2004.10.013. PMID: 15530382.

15: Vecchiato M, Cremonese S, Gregoris E, Barbaro E, Gambaro A, Barbante C. Fragrances as new contaminants in the Venice lagoon. Sci Total Environ. 2016 Oct 1;566-567:1362-1367. doi: 10.1016/j.scitotenv.2016.05.198. Epub 2016 Jun 4. PMID: 27267717.

16: Babcock DF. Development. Smelling the roses? Science. 2003 Mar 28;299(5615):1993-4. doi: 10.1126/science.1083059. PMID: 12663902.

17: Esmaeili A, Afshari S, Esmaeili D. Formation of harmful compounds in biotransformation of lilial by microorganisms isolated from human skin. Pharm Biol. 2015;53(12):1768-73. doi: 10.3109/13880209.2015.1005755. Epub 2015 Apr 9. PMID: 25856710.

18: Kalbe B, Knobloch J, Schulz VM, Wecker C, Schlimm M, Scholz P, Jansen F, Stoelben E, Philippou S, Hecker E, Lübbert H, Koch A, Hatt H, Osterloh S. Olfactory Receptors Modulate Physiological Processes in Human Airway Smooth Muscle Cells. Front Physiol. 2016 Aug 4;7:339. doi: 10.3389/fphys.2016.00339. PMID: 27540365; PMCID: PMC4972829.

19: Veitinger T, Riffell JR, Veitinger S, Nascimento JM, Triller A, Chandsawangbhuwana C, Schwane K, Geerts A, Wunder F, Berns MW, Neuhaus EM, Zimmer RK, Spehr M, Hatt H. Chemosensory Ca2+ dynamics correlate with diverse behavioral phenotypes in human sperm. J Biol Chem. 2011 May 13;286(19):17311-25. doi: 10.1074/jbc.M110.211524. Epub 2011 Mar 21. PMID: 21454470; PMCID: PMC3089573.

20: de March CA, Titlow WB, Sengoku T, Breheny P, Matsunami H, McClintock TS. Modulation of the combinatorial code of odorant receptor response patterns in odorant mixtures. Mol Cell Neurosci. 2020 Apr;104:103469. doi: 10.1016/j.mcn.2020.103469. Epub 2020 Feb 12. PMID: 32061665; PMCID: PMC7138139.

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