gamma-DODECALACTONE - CAS 2305-05-7
Molecular Formula:
C12H22O2
Molecular Weight:
198.31
COA:
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Olfactive Family:
Fatty | Green | Sweet | Waxy
FEMA:
2400
Odor description:
A waxy, fatty, sweet aroma with green rind-like undertones.
Purity:
97.0%
Appearance:
colorless to yellow liquid
Synonyms:
2(3H)-Furanone, dihydro-5-octyl-, 4-Dodecanolide, 4-Hydroxydodecanoic acid, gamma-lactone, 5-Octyldihydrofuran-2(3H)-one, gamma-DODECALACTONE FCC, gamma-Octylbutyrolactone
Solubility:
Insoluble in water; soluble in alcohol.
Storage:
Store tightly sealed under inert gas in a cool, well-ventilated area.
MSDS:
Inquire
Shelf Life:
60 months from manufacture date
Boiling Point:
311.45 C (EPI 4.0)
Specificgravity:
0.933 : 0.938 at 25 deg C
Refractive index:
1.451 : 1.456 at 20 deg C
1.Structure and functions of gamma-dodecalactone isolated from Antrodia camphorata for NK cell activation.
Chen CJ1, Vijaya Krishna R, Tsai CC, Wu WH, Chao LK, Hwang KH, Chien CM, Chang HY, Chen ST. Bioorg Med Chem. 2010 Sep 15;18(18):6896-904. doi: 10.1016/j.bmc.2010.07.024. Epub 2010 Jul 16.
The preserved fungal species Antrodia camphorata has diverse health-promoting effects and has been popularly used in East Asia as a traditional herb. We isolated a volatile compound from the culture medium of A. camphorata and identified it as gamma-dodecalactone (gamma-DDL). Cytomic screening for immune-modulating activity revealed that gamma-DDL can activate human NK cells to express the early activation marker CD69. Further experiments showed that gamma-DDL not only can induce NK cells to express CD69 but also stimulate NK cells to secrete cytotoxic molecules (FasL and granzyme B) and Th1 cytokines (TNF-alpha and INF-gamma). Measuring the distribution of gamma-DDL in the subcellular compartments of NK cells revealed that gamma-DDL has been converted to 4-hydroxydodecanoic acid (an acyclic isomer of gamma-DDL) in a time-dependent manner in the cytoplasm. Synthetic (R,S)-4-hydroxydodecanoic acid activated NK cells to express CD69 mRNA within 10min, in contrast to gamma-DDL, which activated NK cells to express CD69 within 50min.
2.Chirality of the gamma-lactones produced by Sporidiobolus salmonicolor grown in two different media.
Dufossé L1, Féron G, Latrasse A, Guichard E, Spinnler HE. Chirality. 1997;9(7):667-71.
Sporidiobolus salmonicolor is an aroma-producing yeast which gives a peach-like smell to the culture media. The enantiomeric ratios of the five gamma-lactones produced by this yeast cultivated in two different media were determined by multidimensional gas chromatography (MDGC) on a fused silica capillary column coupled to a modified beta-cyclodextrin column. These ratios remain constant during growth and are not affected by the composition of the medium. The (R)-enantiomer is highly predominant (99%) for gamma-decalactone and predominant (68-88%) for gamma-octalactone, gamma-nonalactone, and (Z6)-gamma-dodecenolactone. A ratio close to racemic was found for gamma-dodecalactone. A discussion on the metabolic origin of these lactones is based on the analysis of the enantiomeric ratios obtained. With respect to consumers' preference for products considered as "natural," microbial lactone production may represent a valuable alternative to fruit flavors.
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