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- Caryophyllene (), more formally (−)-β-caryophyllene, (BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature. β-Caryophyllene acts as a full agonist of the Cannabinoid receptor type 2 (CB2 receptor) in rats. β-Caryophyllene has a binding affinity of Ki = 155nM at the CB2 receptors in mice. β-Caryophyllene has been shown to have anti-inflammatory action linked to its CB2 receptor activity in a study comparing the pain killing effects in mice with and without CB2 receptors with the group of mice without CB2 receptors seeing little benefit compared to the mice with functional CB2 receptors. β-Caryophyllene has the highest cannabinoid activity compared to the ring opened isomer α-caryophyllene which may modulate CB2 activity. To compare binding, Cannabinol (CBN) binds to the CB2 receptors as a partial agonist with an affinity of CB2 Ki = 126.4 nM while Delta-9-Tetrahydrocannabinol binds to the CB2 receptors as a partial agonist with an affinity of Ki = 36nM.The first total synthesis of caryophyllene in 1964 by E. J. Corey was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time.Caryophyllene is one of the chemical compounds that contributes to the aroma of black pepper.Caryophyllene has been given GRAS (generally regarded as safe) designation by the FDA and is approved by the FDA for use as a food additive, typically for flavoring.Caryophyllene helps to improve cold tolerance at low ambient temperatures. Wild giant pandas frequently roll in horse manure, which contains beta-caryophyllene/caryophyllene oxide, to inhibit transient receptor potential melastatin 8 (TRPM8), an archetypical cold-activated ion channel of mammals.
- capryl honily
- caprylin holy
- caprylyl hoin
- lar philocyny
- lin polyarchy
- nil polyarchy
- yin pollarchy
- icon phyllary
- cion phyllary
- coin phyllary
- hoin caprylyl
- illy orphancy
- lily orphancy
- yill orphancy
- holy caprylin
- inly polyarch
- liny polyarch
- choil pyranyl
- olchi pyranyl
- choli pyranyl
- pinch royally
- pyin chorally
- piny chorally
- phyla corylin
- haply corylin
- hylic nopalry
- payni chloryl
- orcin aphylly
- corin aphylly
- noric aphylly
- racily phylon
- parchy lionly
- holly cyprina
- holly cyprian
- prancy holily
- phony cyrilla
- phony lyrical
- pylon charily
- cahill noy pry
- cahill noy pyr
- cahill pry yon
- cahill pyr yon
- cain holly pry
- cain holly pyr
- cain hy prolyl
- cairn holy ply
- cairn hy polly
- cairny hy poll
- cairo hyp llyn
- cal holy pirny
- cal honily pry
- cal honily pyr
- cal horny pily
- cal hory pinyl
- cal hory pliny
- cal hyp ironly
- call horny yip
- call hory piny
- call hory pyin
- call hoy pirny
- call hyp irony
- call hypo yirn
- callo hy pirny
- callo hyp yirn
- calor hy pinyl
- calor hy pliny
- calor hyp inly
- calor hyp liny
- calp holy yirn
- calp hory inly
- calp hory liny
- calp hy ironly
- can hilly pory
- can hilly pyro
- can hilly ropy
- can holily pry
- can holily pyr
- can hy pillory
- can hypo rilly
- canopy hy rill
- canroy hy pill
- canroy hyp ill
- cany hi prolyl
- cany hill pory
- cany hill pyro
- cany hill ropy
- cany hilly pro
- cany holly pir
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- cany holy pirl
- cany hop rilly
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- cany hypo rill
- cany lory phil
- cany ory phill
- cany phill roy
- cany phill yor
- cany pho rilly
- cany poh rilly
- cap holly yirn
- cap horny illy
- cap horny lily
- cap horny yill
- caph inly lory
- caph liny lory
- caph noy rilly
- caph rilly yon
- caplin hy lory
- capon hy rilly
- capri hoy llyn
- caproyl hy lin
- caproyl hy nil
- capryl hi lyon
- capryl hi only
- capryl hin loy
- capryl ho inly
- capryl ho liny
- capryl holy in
- capryl hoy lin
- capryl hoy nil
- capryl hy lino
- capryl hy lion
- capryl hy loin
- capryl hy noil
- capryl inly oh
- capryl liny oh
- caprylyl hi no
- caprylyl hi on
- caprylyl ho in
- caprylyl in oh
- car hilly pony
- car holly piny
- car holly pyin
- car holy pinyl
- car holy pliny
- ah ply corylin
- ah only picryl
- ah lyon picryl
- ah lyric pylon
- ah cyril pylon
- ah colly pirny
- ah coryl pinyl
- ah coryl pliny
- ha ply corylin
- ha only picryl
- ha lyon picryl
- ha lyric pylon
- ha cyril pylon
- ha colly pirny
- ha coryl pinyl
- ha coryl pliny
- an yip chloryl
- an holy picryl
- an poly richly
- an ploy richly
- an lory phylic
- an ropy chilly
- an pory chilly
- an pyro chilly
- ach yin prolyl
- ach ply ironly
- ach pry lionly
- ach pyr lionly
- ach yirn polly
- ach lory pinyl
- ach lory pliny
- ach pony rilly
- cha yin prolyl
- cha ply ironly
- cha pry lionly
- cha pyr lionly
- cha yirn polly
- cha lory pinyl
- cha lory pliny
- cha pony rilly
- cal pry honily
- cal pyr honily
- cal pily horny
- lac hyp ironly
- lac pry honily
- lac pyr honily
- lac holy pirny
- lac pily horny
- lac hory pinyl
- lac hory pliny
- can pry holily
- can pyr holily
- can ropy hilly
- can pory hilly
- can pyro hilly
- hi no caprylyl
- hi on caprylyl
- hi col pyranyl
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"caryophyllin." Anagrams.net. STANDS4 LLC, 2024. Web. 1 May 2024. <https://www.anagrams.net/caryophyllin>.
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