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beta-sesquiphellandrene
(S-(R,S))-3-(1,5-dimethyl-4-hexenyl)-6-methylene cyclohexene

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CODE110365 CODE110365
Product(s):
20307-83-9 beta-sesquiPhellandrene

Name:	3-[(2S)-6-methylhept-5-en-2-yl]-6-methylidenecyclohexene
CAS Number:	20307-83-9	3D/inchi
FDA UNII:	Search
XlogP3-AA:	5.40 (est)
Molecular Weight:	204.35628000
Formula:	C15 H24
NMR Predictor:	Predict (works with chrome, Edge or firefox)

Category:natural substances and extractives

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:	Search
Google Books:	Search
Google Scholar: with word "volatile"	Search
Google Scholar: with word "flavor"	Search
Google Scholar: with word "odor"	Search
Google Patents:	Search
US Patents:	Search
EU Patents:	Search
Pubchem Patents:	Search
PubMed:	Search
NCBI:	Search

Physical Properties:

Appearance:	colorless to pale yellow clear liquid (est)
Assay:	96.00 to 100.00
Food Chemicals Codex Listed:	No
Boiling Point:	270.00 to 272.00 °C. @ 760.00 mm Hg
Vapor Pressure:	0.011000 mmHg @ 25.00 °C. (est)
Flash Point:	226.00 °F. TCC ( 107.78 °C. )
logP (o/w):	6.522 (est)
Soluble in:
	alcohol
	water, 0.01283 mg/L @ 25 °C (est)
Insoluble in:
	water

Organoleptic Properties:

Odor Type: herbal

herbal fruity woody

Odor Description:at 100.00 %. herbal fruity woody

Odor and/or flavor descriptions from others (if found).

Cosmetic Information:

None found

Suppliers:

For experimental / research use only.

beta-sesquiPhellandrene

Safety Information:


Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
natural substances and extractives
Recommendation for beta-sesquiphellandrene usage levels up to:
	not for fragrance use.

Recommendation for beta-sesquiphellandrene flavor usage levels up to:
	not for flavor use.

Safety References:

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :5321277

National Institute of Allergy and Infectious Diseases:Data

3-[(2S)-6-methylhept-5-en-2-yl]-6-methylidenecyclohexene

Chemidplus:0020307839

References:

	3-[(2S)-6-methylhept-5-en-2-yl]-6-methylidenecyclohexene
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	5321277
Pubchem (sid):	135231218
Flavornet:	20307-83-9
Pherobase:	View

Other Information:

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
KEGG (GenomeNet):	C16776
HMDB (The Human Metabolome Database):	HMDB36163
FooDB:	FDB015016
YMDB (Yeast Metabolome Database):	YMDB16103
Typical G.C.
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Potential Blenders and core components note

For Odor

acidic

2-

methyl-2-pentenoic acid
FL/FR

alcoholic

fusel oil
FL/FR

anisic

amyl furoate
FL/FR

balsamic

dextro,laevo-iso

iso

bornyl acetate
FL/FR

fir carboxylate
FR

camphoreous

dextro-

caramellic

diethyl malate
FL/FR

earthy

2-

ethereal

ethyl 4-pentenoate
FL/FR

fatty

hexyl pivalate
FR

floral

alpha-

amyl cinnamaldehyde
FL/FR

iso

amyl salicylate
FL/FR

anise indene
FR

benzyl acetone
FL/FR

boronia absolute
FL/FR

butyl tiglate
FR

cassis cyclohexene
FR

dimethyl benzyl carbinyl butyrate
FL/FR

geranyl tiglate
FL/FR

beta-

ionone
FL/FR

jasmin absolute egypt (from concrete)
FL/FR

(Z)-

karo karounde absolute
FR

lavender oil france
FL/FR

lavender oil greece
FL/FR

menthadienyl formate
FR

methyl benzyl acetate (mixed ortho-,meta-,para-)
FL/FR

N-

methyl ionone
FR

alpha-iso

methyl ionone (90% min.)
FL/FR

nonan-3-yl acetate
FL/FR

3-

nonisyl propionate
FR

petitgrain bigarade oil
FL/FR

petitgrain lemon oil
FL/FR

prenyl salicylate
FL/FR

rose undecene
FR

fruity

para-

anisyl propionate
FL/FR

3-

benzyl-4-heptanone
FL/FR

dihydroactinidolide
FL/FR

green acetate
FR

linalool oxide acetates
FL/FR

para-

menth-1-ene-9-ol
FL/FR

2-

methyl butyl isovalerate
FL/FR

green

butyl heptanoate
FL/FR

iso

butyl heptanoate
FL/FR

iso

butyl methyl ketone
FL/FR

iso

cyclocitral (IFF)
FL/FR

hexyl tiglate
FL/FR

para-

methyl hydratropaldehyde
FL/FR

herbal

iso

amyl heptanoate
FL/FR

bornyl 2-methyl butyrate
FL/FR

bornyl butyrate
FL/FR

beta-

bourbonene
FL/FR

buchu mercaptan acetate
FL/FR

butyl levulinate
FL/FR

alpha-

chamomile propionate
FR

chamomile valerate
FR

coriander oleoresin
FL/FR

cuminyl acetate
FL/FR

dimethyl cyclormol (IFF)
FR

herbal undecanone
FR

immortelle flower oil
FL/FR

linalyl octanoate
FL/FR

1-para-

menthen-9-yl acetate
FL/FR

2-

methyl butyl salicylate
FL/FR

methyl cyclogeranate (Firmenich)
FR

methyl hexyl ether
FL/FR

(1S,5R)-

myrtenyl acetate
FL/FR

nonisyl acetate
FR

3-

octanon-1-ol
FL/FR

curled

parsley leaf oil
FL/FR

tagete oil CO2 extract
FL/FR

tagete oil south africa
FL/FR

tagete oil turkey
FL/FR

tagete oil zambia
FL/FR

tea leaf absolute
FL/FR

thyme oil wild or creeping
FL/FR

tricyclodecenyl propionate
FR

viridiflorol
FL/FR

minty

pennyroyal oil
FL/FR

orris

orris capronate
FL/FR

spicy

cinnamon acrolein
FL/FR

clove bud oil
FL/FR

black

currant bud absolute
FL/FR

N,N-

diethyl octanamide
FR

4-iso

propyl-2-cyclohexenone
FL/FR

thujonic

common

tansy leaf oil dutch
FR

woody ketone
FL/FR

woody

(+)-

cistus twig/leaf oil
FL/FR

2-

decalinyl acetate
FR

marine formate
FR

patchouli absolute
FR

polylimonene
FL/FR

spruce needle oil canada
FL/FR

For Flavor

No flavor group found for these

amyl furoate
FL/FR

para-

anisyl propionate
FL/FR

benzyl methyl tiglate
FL

bornyl 2-methyl butyrate
FL/FR

bornyl butyrate
FL/FR

beta-

bourbonene
FL/FR

iso

butyl heptanoate
FL/FR

delta-

alpha-

(+)-

cuminyl acetate
FL/FR

8,9-

dehydrotheaspirone
FL

diethyl malate
FL/FR

ethyl 4-pentenoate
FL/FR

linalool oxide acetates
FL/FR

methyl benzyl acetate (mixed ortho-,meta-,para-)
FL/FR

2-

methyl butyl salicylate
FL/FR

1-

methyl pyrrole
FL

nonan-3-yl acetate
FL/FR

3-

octanon-1-ol
FL/FR

polylimonene
FL/FR

4-iso

propyl-2-cyclohexenone
FL/FR

viridiflorol
FL/FR

woody ketone
FL/FR

acidic

acidic

(E)-2-

hexenoic acid
FL

camphoreous

dextro,laevo-iso

citrus

petitgrain bigarade oil
FL/FR

petitgrain lemon oil
FL/FR

dairy

2-

ethereal

methyl hexyl ether
FL/FR

floral

dimethyl benzyl carbinyl butyrate
FL/FR

geranyl tiglate
FL/FR

jasmin absolute egypt (from concrete)
FL/FR

alpha-iso

methyl ionone (90% min.)
FL/FR

fruity

benzyl acetone
FL/FR

3-

benzyl-4-heptanone
FL/FR

boronia absolute
FL/FR

buchu mercaptan acetate
FL/FR

butyl heptanoate
FL/FR

dihydroactinidolide
FL/FR

fusel oil
FL/FR

linalyl octanoate
FL/FR

1-para-

menthen-9-yl acetate
FL/FR

2-

methyl butyl isovalerate
FL/FR

tagete oil CO2 extract
FL/FR

tagete oil south africa
FL/FR

tagete oil turkey
FL/FR

tagete oil zambia
FL/FR

green

iso

amyl salicylate
FL/FR

iso

butyl methyl ketone
FL/FR

iso

cyclocitral (IFF)
FL/FR

hexyl tiglate
FL/FR

para-

methyl hydratropaldehyde
FL/FR

3-

herbal

iso

amyl heptanoate
FL/FR

butyl levulinate
FL/FR

coriander oleoresin
FL/FR

immortelle flower oil
FL/FR

lavender oil france
FL/FR

lavender oil greece
FL/FR

para-

menth-1-ene-9-ol
FL/FR

curled

parsley leaf oil
FL/FR

prenyl salicylate
FL/FR

thyme oil wild or creeping
FL/FR

medicinal

dextro-

minty

pennyroyal oil
FL/FR

orris

orris capronate
FL/FR

sour

2-

methyl-2-pentenoic acid
FL/FR

spicy

cinnamon acrolein
FL/FR

clove bud oil
FL/FR

black

currant bud absolute
FL/FR

tea

tea leaf absolute
FL/FR

tropical

alpha-

amyl cinnamaldehyde
FL/FR

woody

iso

bornyl acetate
FL/FR

cistus twig/leaf oil
FL/FR

beta-

ionone
FL/FR

(Z)-

(1S,5R)-

myrtenyl acetate
FL/FR

spruce needle oil canada
FL/FR

Potential Uses:

FR	acacia
FR	amber
FR	ambergris
FR	ambreine
FR	amyris
FL/FR	angelica
FR	apple
FR	crabapple
FR	apple green apple
FR	apple red apple
FR	apricot
FR	arnica flower
FL	arrack
FR	ash mountain ash
FR	ash mountain ash berry
FR	banana
FR	bark
FR	basil oil replacer
FR	bayberry
FR	bayberry
FL/FR	beech
FL/FR	benzoin absolute replacer
FR	bergamot
FR	berry
FR	berry jam
FL/FR	birch tar
FR	blackberry
FR	blue grass
FR	blueberry
FR	bois de rose
FR	boronia
FR	boxwood
FR	boxwood berry
FR	boysenberry
FR	bramble arctic bramble blackberry
FL	brandy apricot brandy
FR	bubble gum
FL	buchu leaf
FR	cabreuva wood
FR	cade oil replacer
FL/FR	cajeput
FR	calamus oil replacer
FL/FR	camphor tree bark
FL	capsicum
FL/FR	caraway seed
FR	cardamom oil replacer
FL	carrot
FL/FR	carrot seed
FR	cedar
FR	cedar forest
FR	cedarwood
FR	cedarwood atlas
FR	celery
FR	chamomile
FR	cherry
FR	cherry black cherry
FL	cherry maraschino cherry
FL	cherry wild cherry
FL	chervil
FR	chrysanthemum
FR	cigar
FL/FR	cilantro
FL/FR	cistus
FR	citronella
FR	clary sage oil replacer
FL	cloudberry bakeapple
FL/FR	coriander
FR	costus
FR	cranberry
FL/FR	croton eluteria bark
FL/FR	cubeb
FR	currant
FR	currant black currant
FL/FR	currant bud absolute replacer
FR	currant red currant
FR	cypress oil replacer
FR	date
FR	davana oil replacer
FR	deertongue absolute replacer
FL/FR	dill weed
FR	dogwood
FL	durian
FR	eglantine
FR	elder berry
FR	elder flower
FR	elemi
FR	eucalyptus oil replacer
FR	fennel
FR	fern
FR	fig
FR	fir needle oil replacer
FR	flouve
FR	forest
FR	fruit
	fruit dried fruit
	fruit jam
FR	fruit juicy fruit
FL	fruit punch
FL	fruit tropical fruit
FL/FR	galangal root
FR	galbanum
FR	genet
FL	gin
FR	ginger
FR	ginger white ginger
FR	gingergrass
FR	gooseberry
FR	grape
FR	grape concord grape
FL	grape white grape
FL/FR	guaiacwood
FR	guava
FR	gurjun balsam
FR	hay new mown hay
FR	heather
FR	herbal
FR	hibiscus
FR	hinoki oil replacer
FR	hollyberry
FL	honeydew
FR	hop
FR	huckleberry
FL/FR	hyssop
FL/FR	immortelle
FR	iris blossom
FR	ivy
FL	jackfruit
	jam
FR	juniper
FR	juniper berry
FR	kiwi
FR	labdanum
FR	lavandin
FR	lavender
FL/FR	lavender flower
FL/FR	lavender spike lavender
	loganberry dewberry
FL/FR	lovage root
FL	lychee
FR	mace
FR	maja
FL	mango
FL/FR	marigold
FL/FR	marjoram
FL	mate
	meadow
FR	melissa oil replacer
FR	melon
FR	melon
FL	mimosa
FR	mulberry
FR	myrtle oil replacer
FR	niaouli
FR	oakwood
FR	olibanum
FR	opoponax
FL	orange bitter orange
FR	oregano
FR	orris
FR	osmanthus
FR	papaya
FL	parsley
	parsnip
FR	passion blossom
FR	passion fruit
FR	patchouli
FR	peach
FL	pear
FL	pear bartlett pear
FL	pear emperor pear
FL	pina colada
	pine dwarf pine
FR	pine forest
FR	pineapple
FR	pinion
FR	plum
FL	plum greengage plum
	plum jam
FR	plum mirabelle plum
FR	pomegranate
FR	prune
FR	quince
FL	raisin
FR	raspberry
FR	raspberry black raspberry
	raspberry green raspberry
	raspberry jam
FL	raspberry red raspberry
FR	redwood
FR	reseda
	ripe
	rose wild rose
FR	rosemary
FL/FR	rue
FR	saffron
FR	sandalwood
FL/FR	savin
FR	spikenard oil replacer
FL	spruce
FL	starfruit
FR	strawberry
	strawberry jam
FR	sweet grass
FL	tamarind
FL/FR	tansy oil replacer
FL/FR	tarragon oil replacer
FL	tea
FL	tea black tea
	tea china
FL	tea green tea
FL	tea herbal tea
FL	tea lemon tea
FR	thyme oil white replacer
	timber
FR	tolu balsam
FL	tutti frutti
FL/FR	valerian
FR	vetiver
FL	watermelon
FR	witch hazel
FR	woodruff
FR	woody
FR	wormseed oil replacer
FR	wormwood oil replacer
FR	yew

Occurrence (nature, food, other):note

	alpinia galanga oil @ 1.60% Data GC Search Trop Picture
	boronia absolute @ 0.02% Data GC Search Trop Picture
	cajuput oil vietnam @ trace% Data GC Search Trop Picture
	carrot seed oil @ 0.25% Data GC Search Trop Picture
	ginger rhizome Search Trop Picture
	ginger rhizome oil Search Trop Picture
	ginger root oil Search Trop Picture
	ginger root oil brazil @ 7.00% Data GC Search Trop Picture
	ginger root oil CO2 extract @ 6.81% Data GC Search Trop Picture
	ginger root oil CO2 extract australia @ 8.18% Data GC Search Trop Picture
	jambu flower oil brazil @ 0.10% Data GC Search Trop Picture
	lime oil expressed florida @ trace% Data GC Search Trop Picture
	mandarin fruit Search Trop Picture
	mayur pankh fruit oil himalaya @ 0.70% Data GC Search Trop Picture
	oregano plant Search Trop Picture
	parsley leaf Search Trop Picture
	parsley leaf oil @ 8.51% Data GC Search Trop Picture
	parsley leaf oil cuba @ 1.04% Data GC Search Trop Picture
	rosemary Search Trop Picture
	tea leaf Search Trop Picture
	thymus richardii pers. subsp. nitidus (guss.) jalas oil italy @ 0.70% Data GC Search Trop Picture
	turmeric rhizome Search Trop Picture
	turmeric root oil CO2 extract @ 3.17% Data GC Search Trop Picture
	turmeric root oil vietnam @ 3.00% Data GC Search Trop Picture

Synonyms:

(S-(R,S))-3-(1,5-	dimethyl-4-hexenyl)-6-methylene cyclohexene
(R)-3-	methylene-6-((S)-6-methyl hept-5-en-2-yl) cyclohex-1-ene
3-[(2S)-6-	methylhept-5-en-2-yl]-6-methylidenecyclohexene

Articles:

PubMed:Psychoneuropharmacological activities and chemical composition of essential oil of fresh fruits of Piper guineense (Piperaceae) in mice.

PubMed:Medicinal plants from the genus Acalypha (Euphorbiaceae)--a review of their ethnopharmacology and phytochemistry.

PubMed:Evaluation of chemical profile and antioxidant activity of Tripleurospermum insularum, a new species from Turkey.

PubMed:Chemical composition, antimicrobial and antioxidant activities of the essential oil of Psammogetoncanescens.

PubMed:Engineering the lactococcal mevalonate pathway for increased sesquiterpene production.

PubMed:Functional characterization of sesquiterpene synthase from Polygonum minus.

PubMed:Chemical composition, antioxidant, anti-inflammatory and anti-proliferative activities of essential oils of plants from Burkina Faso.

PubMed:Chemical composition and biological activity of Conyza bonariensis essential oil collected in Mérida, Venezuela.

PubMed:Variability of the root essential oils of Seseli rigidum Waldst. & Kit. (Apiaceae) from different populations in Serbia.

PubMed:[Influence of processing methods on the chemical composition of the essential oil from Aucklandia lappa].

PubMed:Overexpressing 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMGR) in the lactococcal mevalonate pathway for heterologous plant sesquiterpene production.

PubMed:Suites of terpene synthases explain differential terpenoid production in ginger and turmeric tissues.

PubMed:Chemical constituents of the leaf of Alpinia mutica Roxb.

PubMed:Differences in the volatile compositions of ginseng species (Panax sp.).

PubMed:Chemotypification of Astrantia major L. (Apiaceae): essential-oil and lignan profiles of fruits.

PubMed:Essential oil of Curcuma longa inhibits Streptococcus mutans biofilm formation.

PubMed:A single amino acid determines the site of deprotonation in the active center of sesquiterpene synthases SbTPS1 and SbTPS2 from Sorghum bicolor.

PubMed:Pheromonal cross-attraction in true bugs (Heteroptera): attraction of Piezodorus hybneri (Pentatomidae) to its pheromone versus the pheromone of Riptortus pedestris (Alydidae).

PubMed:Chemical composition of the essential oil of aerial parts of Haussknechtia elymaitica Boiss. from Iran: a good natural source for trans-asaron.

PubMed:Distribution and chemical polymorphism of the essential oils of Achillea cartilaginea growing wild in Lithuania.

PubMed:Dynamic evolution of herbivore-induced sesquiterpene biosynthesis in sorghum and related grass crops.

PubMed:Chemical compositions of the rhizome oils of two Alpinia species of Malaysia.

PubMed:Invasion inhibitors of human fibrosarcoma HT 1080 cells from the rhizomes of Zingiber cassumunar: structures of phenylbutanoids, cassumunols.

PubMed:Behavioral responses of the leafhopper, Cicadulina storeyi China, a major vector of maize streak virus, to volatile cues from intact and leafhopper-damaged maize.

PubMed:Free radical scavenging activity and characterization of sesquiterpenoids in four species of Curcuma using a TLC bioautography assay and GC-MS analysis.

PubMed:Chemical composition and antibacterial activity of essential oils of Tripleurospermum disciforme in three developmental stages.

PubMed:Immunotoxicity activity of the major essential oils of Valeriana fauriei Briq against Aedes aegypti L.

PubMed:Chemical composition of the essential oils from the roots of Erigeron acris L. and Erigeron annuus (L.) Pers.

PubMed:[Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry].

PubMed:[Characterization of chemical components of essential oil from flowers of Chrysanthemum morifolium produced in Anhui province].

PubMed:The chemical volatiles (semiochemicals) produced by neotropical stink bugs (Hemiptera: Pentatomidae).

PubMed:Chemical composition of the essential oil of Elephantopus scaber from Southern China.

PubMed:Antimicrobial Activities of Essential Oil and Methanol Extract of Teucrium montanum.

PubMed:[Analysis of volatile oil in herb of pimpinella candolleana by SPME-GC-MS].

PubMed:A male-produced sex pheromone from the neotropical redbanded stink bug, Piezodorus guildinii (W).

PubMed:An evaluation of the allelopathic potential of selected perennial groundcovers: foliar volatiles of catmint (Nepeta x faassenii) inhibit seedling growth.

PubMed:Development of gas chromatography-mass spectrometry with microwave distillation and simultaneous solid-phase microextraction for rapid determination of volatile constituents in ginger.

PubMed:Essential oil composition of diploid and tetraploid clones of ginger (Zingiber officinale Roscoe) grown in Australia.

PubMed:Analysis of leaf surface sesquiterpenes in potato varieties.

PubMed:Chemical composition, antimicrobial and antioxidant activity of the essential oil of Teucrium marum (Lamiaceae).

PubMed:Identification of an EcoRI restriction site for a rapid and precise determination of beta-asarone-free Acorus calamus cytotypes.

PubMed:Analysis by gas chromatography-mass spectrometry of the essential oil from the aerial parts of Pimpinella junoniae Ceb. & Ort., gathered in La Gomera, Canary Islands, Spain.

PubMed:Zingiberene and curcumene in wild tomato.

PubMed:[Chemical constituents in volatile oil from the flos of Dendranthema indicum var. aromaticum var. nov].

PubMed:Sex attractant pheromone of the red-shouldered stink bug Thyanta pallidovirens: a pheromone blend with multiple redundant components.

PubMed:[Determination of chemical constituents of the volatile oil from Curcuma longa by gas chromatography-mass spectrometry].

PubMed:[Study on chemical constituents of Dendranthema morifolium by GC-MS].

PubMed:Molecular cloning, expression, and characterization of amorpha-4,11-diene synthase, a key enzyme of artemisinin biosynthesis in Artemisia annua L.

PubMed:Isolation of antirhinoviral sesquiterpenes from ginger (Zingiber officinale).

PubMed:[Terpenoids and curcuminoids of the rhizoma of Curcuma xanthorrhiza Roxb].

PubMed:[Stomachic principles in ginger. II. Pungent and anti-ulcer effects of low polar constituents isolated from ginger, the dried rhizoma of Zingiber officinale Roscoe cultivated in Taiwan. The absolute stereostructure of a new diarylheptanoid].

PubMed:Essential Oils of Achillea ptarmica.

PubMed:The essential oil from Thymus praecox ssp. arcticus growing in Iceland.

Notes:

Constit. of the oil of ginger (Zingiber officinale)

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