Germacrene D | CAS# 37839-63-7 | Antioxidant Essential Oil

MedKoo Cat#: 564538 | Name: Germacrene D

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Description:

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

Germacrene D is a natural essential oil with antioxidant activity and cytotoxicity on tumour cells.

Chemical Structure

Germacrene D

CAS#37839-63-7

Theoretical Analysis

MedKoo Cat#: 564538

Name: Germacrene D

CAS#: 37839-63-7

Chemical Formula: C15H24

Exact Mass: 204.1878

Molecular Weight: 204.36

Elemental Analysis: C, 88.16; H, 11.84

Price and Availability

Size	Price	Availability
1mg	USD 450.00	2 Weeks
5mg	USD 1,050.00	2 Weeks
10mg	USD 1,650.00	2 Weeks

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Related CAS #

No Data

Synonym

1(10),4(14),5-Germacratriene; Germacrene D

IUPAC/Chemical Name

(S,1Z,6Z)-8-Isopropyl-1-methyl-5-methylenecyclodeca-1,6-diene

InChi Key

GAIBLDCXCZKKJE-ACWLMNNXSA-N

InChi Code

InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8-,14-7-/t15-/m0/s1

SMILES Code

C=C1CC/C=C(C)\CC[C@@H](C(C)C)/C=C\1

Appearance

Clear oil

Purity

>98% (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

2934.99.03.00

More Info

Certificate of Analysis

View CoA: current batch, Lot#A22O02B04

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 204.36 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

1: Noge K, Shimizu N, Becerra JX. (R)-(-)-linalyl acetate and (S)-(-)-germacrene D from the leaves of Mexican Bursera linanoe. Nat Prod Commun. 2010 Mar;5(3):351-4. PubMed PMID: 20420305. 2: Noge K, Becerra JX. Germacrene D, a common sesquiterpene in the genus Bursera (Burseraceae). Molecules. 2009 Dec 15;14(12):5289-97. doi: 10.3390/molecules14125289. PubMed PMID: 20032892. 3: Setzer WN. Germacrene D cyclization: an Ab initio investigation. Int J Mol Sci. 2008 Jan;9(1):89-97. Epub 2008 Jan 25. PubMed PMID: 19325722; PubMed Central PMCID: PMC2635598. 4: Picaud S, Olsson ME, Brodelius M, Brodelius PE. Cloning, expression, purification and characterization of recombinant (+)-germacrene D synthase from Zingiber officinale. Arch Biochem Biophys. 2006 Aug 1;452(1):17-28. Epub 2006 Jun 21. PubMed PMID: 16839518. 5: Jiang J, He X, Cane DE. Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin. J Am Chem Soc. 2006 Jun 28;128(25):8128-9. PubMed PMID: 16787064. 6: Yoshikuni Y, Martin VJ, Ferrin TE, Keasling JD. Engineering cotton (+)-delta-cadinene synthase to an altered function: germacrene D-4-ol synthase. Chem Biol. 2006 Jan;13(1):91-8. PubMed PMID: 16426975. 7: Prosser I, Altug IG, Phillips AL, König WA, Bouwmeester HJ, Beale MH. Enantiospecific (+)- and (-)-germacrene D synthases, cloned from goldenrod, reveal a functionally active variant of the universal isoprenoid-biosynthesis aspartate-rich motif. Arch Biochem Biophys. 2004 Dec 15;432(2):136-44. PubMed PMID: 15542052. 8: Lücker J, Bowen P, Bohlmann J. Vitis vinifera terpenoid cyclases: functional identification of two sesquiterpene synthase cDNAs encoding (+)-valencene synthase and (-)-germacrene D synthase and expression of mono- and sesquiterpene synthases in grapevine flowers and berries. Phytochemistry. 2004 Oct;65(19):2649-59. PubMed PMID: 15464152. 9: Umlauf D, Zapp J, Becker H, Adam KP. Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae). Phytochemistry. 2004 Sep;65(17):2463-70. PubMed PMID: 15381410. 10: He X, Cane DE. Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2). J Am Chem Soc. 2004 Mar 10;126(9):2678-9. PubMed PMID: 14995166. 11: Arimura G, Huber DP, Bohlmann J. Forest tent caterpillars (Malacosoma disstria) induce local and systemic diurnal emissions of terpenoid volatiles in hybrid poplar (Populus trichocarpa x deltoides): cDNA cloning, functional characterization, and patterns of gene expression of (-)-germacrene D synthase, PtdTPS1. Plant J. 2004 Feb;37(4):603-16. PubMed PMID: 14756770. 12: Stranden M, Liblikas I, König WA, Almaas TJ, Borg-Karlson AK, Mustaparta H. (-)-Germacrene D receptor neurones in three species of heliothine moths: structure-activity relationships. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2003 Jul;189(7):563-77. Epub 2003 Jun 25. PubMed PMID: 12827423. 13: Gioacchini AM, Menotta M, Polidori E, Giomaro G, Stocchi V. Solid-phase microextraction gas chromatography/ion trap mass spectrometry and multistage mass spectrometry experiments in the characterization of germacrene D. J Mass Spectrom. 2002 Dec;37(12):1229-35. PubMed PMID: 12489082. 14: Mozuraitis R, Stranden M, Ramirez MI, Borg-Karlson AK, Mustaparta H. (-)-Germacrene D increases attraction and oviposition by the tobacco budworm moth Heliothis virescens. Chem Senses. 2002 Jul;27(6):505-9. PubMed PMID: 12142326. 15: Steliopoulos P, Wüst M, Adam KP, Mosandl A. Biosynthesis of the sesquiterpene germacrene D in Solidago canadensis: 13C and (2)H labeling studies. Phytochemistry. 2002 May;60(1):13-20. PubMed PMID: 11985846. 16: Stranden M, Borg-Karlson AK, Mustaparta H. Receptor neuron discrimination of the germacrene D enantiomers in the moth Helicoverpa armigera. Chem Senses. 2002 Feb;27(2):143-52. PubMed PMID: 11839612. 17: Bülow N, Konig WA. The role of germacrene D as a precursor in sesquiterpene biosynthesis: investigations of acid catalyzed, photochemically and thermally induced rearrangements. Phytochemistry. 2000 Sep;55(2):141-68. PubMed PMID: 11065290. 18: Røstelien T, Borg-Karlson AK, Fäldt J, Jacobsson U, Mustaparta H. The plant sesquiterpene germacrene D specifically activates a major type of antennal receptor neuron of the tobacco budworm moth Heliothis virescens. Chem Senses. 2000 Apr;25(2):141-8. PubMed PMID: 10781020. 19: Schmidt CO, Bouwmeester HJ, de Kraker JW, König WA. Biosynthesis of (+)- and (-)-Germacrene D in Solidago canadensis: Isolation and Characterization of Two Enantioselective Germacrene D Synthases. Angew Chem Int Ed Engl. 1998 Jun 5;37(10):1400-1402. doi: 10.1002/(SICI)1521-3773(19980605)37:10<1400::AID-ANIE1400>3.0.CO;2-I. PubMed PMID: 29710884. 20: Tsuchiya Y, Matsumoto A, Shudo K, Okamoto T. [Identification of germacrene-D, one of the volatile metabolities produced by Actinomycetes (author's transl)]. Yakugaku Zasshi. 1980 Apr;100(4):468-71. Japanese. PubMed PMID: 7431217.