Santalene

• CAT Number: I035982
• CAS Number: 512-61-8
• Molecular Formula: C15H24
• Molecular Weight: 204.35
• Purity: 98%
• Solubility: Soluble in DMSO
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 1,7-dimethyl-7-(4-methylpent-3-en-1-yl)tricyclo[2.2.1.02,6]heptane
• InChI: InChI=1S/C15H24/c1-10(2)6-5-7-14(3)11-8-12-13(9-11)15(12,14)4/h6,11-13H,5,7-9H2,1-4H3
• InChIKey: KWFJIXPIFLVMPM-UHFFFAOYSA-N
• SMILES: C/C(C)=C/CCC1(C)C2(C)C3CC1CC23

Santalene (Cat.No:I035982) is a natural sesquiterpene alcohol found in sandalwood oil, known for its pleasant woody and aromatic scent. It is commonly used in perfumery and aromatherapy due to its soothing and calming properties. Santalene has also been studied for potential therapeutic benefits in traditional medicine and cosmetics.

Reference

1: Zhan X, Zhang YH, Chen DF, Simonsen HT. Metabolic engineering of the moss Physcomitrella patens to produce the sesquiterpenoids patchoulol and α/β-santalene. Front Plant Sci. 2014 Nov 18;5:636. doi: 10.3389/fpls.2014.00636. eCollection 2014. PubMed PMID: 25477891; PubMed Central PMCID: PMC4235272.
2: Jindal G, Sunoj RB. Revisiting sesquiterpene biosynthetic pathways leading to santalene and its analogues: a comprehensive mechanistic study. Org Biomol Chem. 2012 Oct 21;10(39):7996-8006. PubMed PMID: 22951817.
3: Tippmann S, Scalcinati G, Siewers V, Nielsen J. Production of farnesene and santalene by Saccharomyces cerevisiae using fed-batch cultivations with RQ-controlled feed. Biotechnol Bioeng. 2016 Jan;113(1):72-81. doi: 10.1002/bit.25683. Epub 2015 Sep 2. PubMed PMID: 26108688.
4: Scalcinati G, Partow S, Siewers V, Schalk M, Daviet L, Nielsen J. Combined metabolic engineering of precursor and co-factor supply to increase α-santalene production by Saccharomyces cerevisiae. Microb Cell Fact. 2012 Aug 31;11:117. doi: 10.1186/1475-2859-11-117. PubMed PMID: 22938570; PubMed Central PMCID: PMC3527295.
5: Jones CG, Moniodis J, Zulak KG, Scaffidi A, Plummer JA, Ghisalberti EL, Barbour EL, Bohlmann J. Sandalwood fragrance biosynthesis involves sesquiterpene synthases of both the terpene synthase (TPS)-a and TPS-b subfamilies, including santalene synthases. J Biol Chem. 2011 May 20;286(20):17445-54. doi: 10.1074/jbc.M111.231787. Epub 2011 Mar 24. Erratum in: J Biol Chem. 2012 Nov 2;287(45):37713-4. PubMed PMID: 21454632; PubMed Central PMCID: PMC3093818.
6: Rani A, Ravikumar P, Reddy MD, Kush A. Molecular regulation of santalol biosynthesis in Santalum album L. Gene. 2013 Sep 25;527(2):642-8. doi: 10.1016/j.gene.2013.06.080. Epub 2013 Jul 13. PubMed PMID: 23860319.
7: Scalcinati G, Knuf C, Partow S, Chen Y, Maury J, Schalk M, Daviet L, Nielsen J, Siewers V. Dynamic control of gene expression in Saccharomyces cerevisiae engineered for the production of plant sesquitepene α-santalene in a fed-batch mode. Metab Eng. 2012 Mar;14(2):91-103. doi: 10.1016/j.ymben.2012.01.007. Epub 2012 Feb 8. PubMed PMID: 22330799.
8: Hodgson GL, MacSweeney DF, Money T. Synthesis of campherenone, epicampherenone, beta-santalene, epi-beta-santalene, alpha-santalene, ylangocamphor, copacamphor, and sativene. J Chem Soc Perkin 1. 1973;19:2113-30. PubMed PMID: 4796661.
9: Couleric P, Thouvenot L, Nour M, Asakawa Y. Chemical Originalities of New Caledonian Liverworts from Lejeuneaceae Family. Nat Prod Commun. 2015 Sep;10(9):1501-4. PubMed PMID: 26594744.
10: Celedon JM, Chiang A, Yuen MM, Diaz-Chavez ML, Madilao LL, Finnegan PM, Barbour EL, Bohlmann J. Heartwood-specific transcriptome and metabolite signatures of tropical sandalwood (Santalum album) reveal the final step of (Z)-santalol fragrance biosynthesis. Plant J. 2016 May;86(4):289-99. doi: 10.1111/tpj.13162. Epub 2016 Apr 15. PubMed PMID: 26991058.
11: Raina AP, Negi KS. Essential oil composition of valeriana jatamansi jones from himalayan regions of India. Indian J Pharm Sci. 2015 Mar-Apr;77(2):218-22. PubMed PMID: 26009656; PubMed Central PMCID: PMC4442472.
12: Diaz-Chavez ML, Moniodis J, Madilao LL, Jancsik S, Keeling CI, Barbour EL, Ghisalberti EL, Plummer JA, Jones CG, Bohlmann J. Biosynthesis of Sandalwood Oil: Santalum album CYP76F cytochromes P450 produce santalols and bergamotol. PLoS One. 2013 Sep 18;8(9):e75053. doi: 10.1371/journal.pone.0075053. eCollection 2013. PubMed PMID: 24324844; PubMed Central PMCID: PMC3854609.
13: Verdan MH, Ehrenfried CA, Scharf DR, Cervi AC, Salvadore MJ, Barison A, Stefanello EA. Chemical Constituents from Sinningia canescens and S. warmingii. Nat Prod Commun. 2014 Oct;9(10):1535-7. PubMed PMID: 25522555.
14: Martins RL, Simões RC, Rabelo ÉM, Farias AL, Rodrigues AB, Ramos RD, Fernandes JB, Santos LD, de Almeida SS. Chemical Composition, an Antioxidant, Cytotoxic and Microbiological Activity of the Essential Oil from the Leaves of Aeollanthus suaveolens Mart. ex Spreng. PLoS One. 2016 Dec 1;11(12):e0166684. doi: 10.1371/journal.pone.0166684. eCollection 2016. PubMed PMID: 27907002; PubMed Central PMCID: PMC5132230.
15: Zi J, Matsuba Y, Hong YJ, Jackson AJ, Tantillo DJ, Pichersky E, Peters RJ. Biosynthesis of lycosantalonol, a cis-prenyl derived diterpenoid. J Am Chem Soc. 2014 Dec 10;136(49):16951-3. doi: 10.1021/ja508477e. Epub 2014 Nov 21. PubMed PMID: 25406026; PubMed Central PMCID: PMC4277783.
16: Wang Y, Wen M, Li M, Zhao J, Han X. [Progress in biosynthesis of santalene and santalol]. Sheng Wu Gong Cheng Xue Bao. 2018 Jun 25;34(6):862-875. doi: 10.13345/j.cjb.170465. Chinese. PubMed PMID: 29943532.
17: Daramwar PP, Srivastava PL, Priyadarshini B, Thulasiram HV. Preparative separation of α- and β-santalenes and (Z)-α- and (Z)-β-santalols using silver nitrate-impregnated silica gel medium pressure liquid chromatography and analysis of sandalwood oil. Analyst. 2012 Oct 7;137(19):4564-70. doi: 10.1039/c2an35575b. PubMed PMID: 22900258.
18: PREMA BR, BHATTACHRYYA PK. Microbiological transformations of terpenes. III. Transformations of some mono- and sesqui-terpenes. Appl Microbiol. 1962 Nov;10:529-31. PubMed PMID: 13986020; PubMed Central PMCID: PMC1057908.
19: Srivastava PL, Daramwar PP, Krithika R, Pandreka A, Shankar SS, Thulasiram HV. Functional Characterization of Novel Sesquiterpene Synthases from Indian Sandalwood, Santalum album. Sci Rep. 2015 May 15;5:10095. doi: 10.1038/srep10095. PubMed PMID: 25976282; PubMed Central PMCID: PMC4432371.
20: Chen Y, Daviet L, Schalk M, Siewers V, Nielsen J. Establishing a platform cell factory through engineering of yeast acetyl-CoA metabolism. Metab Eng. 2013 Jan;15:48-54. doi: 10.1016/j.ymben.2012.11.002. Epub 2012 Nov 17. PubMed PMID: 23164578.